N-substituted perhydrodiazine

ABSTRACT

N-substituted perhydro-2,3-diazines of the formula I                    
     in which the variables Z, R, m and R A  are as defined in claim 1, a process for their preparation and the use of the compounds of the formula I as starting materials for preparing herbicides of the formula V                    
     in which R, R A , Z and m are as defined above, X is O or S and Q is a C 6 -C 14 -aromatic radical are described.

The present invention relates to 1-oxa- and 1-thia-3,4-diazines which are substituted in the 4-position, to a process for their preparation and to their use in a process for preparing novel herbicidally active compounds.

WO 94/10173 discloses perhydrogenated 1-oxa-3,4-diazines of the formula A in which Z is S, O, S═O or SO₂ and Q is a C₆-C₁₄-aromatic radical. The compounds A are used as starting materials for preparing herbicides with triazoline-2,5-dione structure (Compounds B).

The compounds of the formula A for their part are prepared by cyclization of substituted N-(N′-arylcarbamoyl)hydrazinoethanols or -thiols with formaldehyde under acidic reaction conditions. The yields of such cyclization reactions are not satisfactory.

In another invention, which is the subject of a parallel application, it has surprisingly been found that compounds of the formula A′

in which Z, X and Q are as defined above and R is a radical which is different from hydrogen have herbicidal activity. Such compounds should be preparable from perhydro-1-oxa- or perhydro-1-thia-3,4-diazines which are substituted in the 4-position at the nitrogen. It was an object of the present invention to provide oxa- and thiadiazines which are substituted in the 4-position at the nitrogen.

We have found that this object is achieved by a process which allows the preparation of 1-oxa- and 1-thia-3,4-diazines which are substituted in the 4-position at the nitrogen in good yields if the substituent located in the 4-position has the meanings given below for R.

Thus, the present invention relates to N-substituted perhydro-3,4-diazines of the formula I

in which the variables Z, R, m and R^(A) are as defined below:

Z is O, S, S═O or SO₂;

R^(A) is hydroxyl, CO₂R¹, halogen, cyano, C(O)NR¹ ₂, OR², C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₃-C₆-alkenyl, C₃-C₆-alkynyl, COR¹, S(O)_(n)R¹ where n=0, 1 or 2, or C(O)SR¹;

R is CO₂H, CHO, CN, C(O)OR³, C(S)OR³, C(O)SR³, C(S)SR³, C(O)NR⁴R⁵, C(S)NR⁴R⁵, C(O)NHCO₂R⁶, C(O)NHSO₂R⁶, C(O)NHSO₃R⁶, C(O)R², P(O)R¹OR¹, P(O)(OR¹)₂, S(O)_(n)R² where n=0, 1, or 2 or SO₂NHR¹;

m has the value 0, 1, 2 or 3

and in which the variables R¹ to R⁷ are as defined below:

R¹ is hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₃-alkoxy-C₁-C₃-alkyl, C₃-C₆-alkenyl or C₃-C₆-alkynyl;

R² is C₁-C₆-alkyl, C₃-C₆-cycloalkyl, C₃-C₆-alkenyl, C₃-C₆-alkynyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy-C₁-C₆-alkyl, hydroxycarbonyl-C₁-C₆-alkyl, C₁-C₆-alkoxycarbonyl-C₁-C₆-alkyl, C₁-C₆-alkylthio-C₁-C₆-alkyl, C₁-C₆-alkylsulfinyl-C₁-C₆-alkyl, C₁-C₆-alkylsulfonyl-C₁-C₆-alkyl, C₃-C₆-cycloalkyl-C₁-C₆-alkyl, C₃-C₆-alkenyloxycarbonyl-C₁-C₆-alkyl, C₃-C₆-alkynyloxycarbonyl-C₁-C₆-alkyl, C₃-C₆-cycloalkoxy-C₁-C₆-alkyl, C₃-C₆-alkenyloxy-C₁-C₆-alkyl, C₃-C₆-alkynyloxy-C₁-C₆-alkyl, C₁-C₆-haloalkoxy-C₁-C₆-alkyl, C₃-C₆-haloalkenyloxy-C₁-C₆-alkyl, C₃-C₆-haloalkynyloxy-C₁-C₆-alkyl, C₃-C₆-cycloalkyl-C₁-C₆-thioalkyl, C₃-C₆-alkenylthio-C₁-C₆-alkyl, C₃-C₆-alkynylthio-C₁-C₆-alkyl, cyano-C₁-C₆-alkyl, C₃-C₆-halocycloalkyl-C₁-C₆-alkyl, halo-C₂-C₆-alkenyl, C₁-C₆-alkoxy-C₃-C₆-alkenyl, C₁-C₆-haloalkoxy-C₃-C₆-alkenyl, C₁-C₆-alkylthio-C₃-C₆-alkenyl, C₃-C₆-haloalkynyl, C₁-C₆-alkoxy-C₃-C₆-alkynyl, C₁-C₆-haloalkoxy-C₃-C₆-alkynyl, C₁-C₆-alkylthio-C₃-C₆-alkynyl, C₁-C₆-alkylcarbonyl, CHR¹COR⁷, CHR¹P(O)(OR⁷)₂, P(O)(OR⁷)₂, CHR¹P(S)(OR⁷)₂, CHR¹C(O)NR⁴R⁵, CHR¹C(O)NH₂,

is phenyl, pyridyl, benzyl, phenoxy-C₁-C₆-alkyl, benzyloxy-C₁-C₆-alkyl, where the phenyl or pyridyl groups of the five last-mentioned substituents may be substituted by halogen, C₁-C₄-alkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkyl,

R³ is C₁-C₁₅-alkyl, C₃-C₈-cycloalkyl, C₂-C₁₀-alkenyl, C₃-C₁₀-alkynyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy-C₁-C₆-alkyl, C₁-C₆-alkylthio-C₁-C₆-alkyl, C₁-C₆-alkylsulfinyl-C₁-C₆-alkyl, C₁-C₆-alkylsulfonyl-C₁-C₆-alkyl, C₁-C₃-alkoxy-C₁-C₃-alkoxy-C₁-C₃-alkyl, C₃-C₆-cycloalkyl-C₁-C₆-alkyl, carboxyl-C₁-C₆-alkyl, C₁-C₆-alkoxycarbonyl-C₁-C₆-alkyl, C₁-C₆-alkoxycarbonyl-C₂-C₆-alkenyl, C₃-C₆-alkenyloxycarbonyl-C₁-C₆-alkyl, C₃-C₆-alkynyloxycarbonyl-C₁-C₆-alkyl, C₃-C₈-cycloalkoxy-C₁-C₆-alkyl, C₃-C₆-alkenyloxy-C₁-C₆-alkyl, C₃-C₆-alkynyloxy-C₁-C₆-alkyl, C₁-C₆-haloalkoxy-C₁-C₆-alkyl, C₃-C₆-haloalkenyloxy-C₁-C₆-alkyl, C₃-C₆-haloalkynyloxy-C₁-C₆-alkyl, C₃-C₆-cycloalkyl-C₁-C₆-thioalkyl, C₃-C₆-alkenylthio-C₁-C₆-alkyl, C₃-C₆-alkynylthio-C₁-C₆-alkyl, cyano-C₁-C₆-alkyl, C₃-C₆-halocycloalkyl-C₁-C₆-alkyl, halo-C₃-C₆-alkenyl, C₁-C₆-alkoxy-C₃-C₆-alkenyl, C₁-C₆-haloalkoxy-C₃-C₆-alkenyl, C₁-C₆-alkylthio-C₃-C₆-alkenyl, C₃-C₆-haloalkynyl, C₁-C₆-alkoxy-C₃-C₆-alkynyl, C₁-C₆-haloalkoxy-C₃-C₆-alkynyl, C₁-C₆-alkylthio-C₃-C₆-alkynyl,

is CHR¹COR⁷, CHR¹P(O)(OR⁷)₂, P(O)(OR⁷)₂, CHR¹P(S)(OR⁷)₂,CHR¹C(O)NR⁴R⁵, CHR¹C(O)NH₂, phenoxy-C₁-C₆-alkyl, benzyloxy-C₁-C₆-alkyl, where the phenyl groups of the two last-mentioned substituents may be substituted by halogen, C₁-C₄-alkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkyl; is phenyl, pyridyl, naphthyl, quinolyl, quinazolyl, quinoxalyl, 1-methylindolyl, 1-methylbenzimidazolyl, 2-methylindazolyl, benzofuranyl, benzothienyl, benzoxazolyl, benzthiazolyl, benzyl, where the 14 last-mentioned substituents may carry, in adjacent positions, a divalent substituent, such as methylenedioxy, difluoromethylenedioxy, chlorofluoromethylenedioxy, dichloromethylenedioxy, or may in each case be mono- to pentasubstituted by halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio, amino, C₁-C₄-monoalkylamino, C₁-C₄-dialkylamino, C₃-C₆-cycloalkyl, C₁-C₄-alkoxycarbonyl, C₁-C₄-alkoxycarbonyl-C₁-C₄-alkyl, hydroxyl, nitro or cyano;

R⁴ is hydrogen, C₁-C₆-alkyl or C₁-C₆-alkoxy;

R⁵, R⁶ independently of one another are hydrogen, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy-C₁-C₆-alkyl, C₁-C₆-alkoxycarbonyl-C₁-C₆-alkyl,

are C₁-C₆-alkoxycarbonyl-C₂-C₆-alkenyl, where the alkenyl chain may additionally carry one to three halogen and/or cyano radicals,

are benzyl which, in adjacent positions of the phenyl ring, may carry a divalent substituent, such as methylenedioxy, difluoromethylenedioxy, chlorofluoromethylenedioxy, dichloromethylenedioxy, or which may be mono- to pentasubstituted by halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio, C₃-C₆-cycloalkyl, C₁-C₄-alkoxycarbonyl, C₁-C₄-alkoxycarbonyl-C₁-C₄-alkyl, hydroxyl, nitro or cyano, or

R⁴ and R⁵ together with the nitrogen atom to which they are attached are a saturated or unsaturated 4- to 7-membered azaheterocycle which, in addition to carbon ring members, may, if desired, contain one of the following members: —O—, —S—, —N═, —NH— or N—(C₁-C₆-alkyl)—;

R⁷ is hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₃-alkoxy-C₁-C₃-alkyl, C₂-C₆-cyanoalkyl, C₃-C₆-alkenyl or C₃-C₆-alkynyl.

The organic molecule moieties mentioned in the definition of R, R^(A), R¹ to R⁷ and at phenyl, cycloalkyl and heterocyclyl rings are collective terms for individual enumerations of the individual group members. All carbon chains, i.e. all (unsubstituted or substituted) alkyl, alkenyl or alkynyl moieties can be straight-chain or branched.

Halogenated substituents preferably carry one, two, three, four or five identical or different halogen atoms or are perhalogenated.

The term halogen denotes in each case fluorine, bromine, chlorine or iodine, in particular fluorine or chlorine.

Examples of other meanings are:

C₁-C₄-alkyl: CH₃, C₂H₅, n-propyl, CH(CH₃)₂, n-butyl, CH(CH₃)—C₂H₅, 2-methylpropyl or C(CH₃)₃, in particular CH₃, C₂H₅ or CH(CH₃)₂;

C₁-C₆-alkyl: C₁-C₄-alkyl as mentioned above, and also, for example, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl or 1-ethyl-2-methylpropyl, in particular CH₃, C₂H₅, n-propyl, CH(CH₃)₂, n-butyl, C(CH₃)₃, n-pentyl or n-hexyl;

C₁-C₁₅-alkyl: C₁-C₆-alkyl as mentioned above, and also, for example, n-heptyl, 1-methylhexyl, 2-methylhexyl, 3-methylhexyl, 4-methylhexyl, 5-methylhexyl, 1-ethylpentyl, 2-ethylpentyl, 3-ethylpentyl, 4-ethylpentyl, 1,1-dimethylpentyl, 1,2-dimethylpentyl, 1,3-dimethylpentyl, 1,4-dimethylpentyl, n-octyl, 1-methylheptyl, 2-methylheptyl, 3-methylheptyl, 4-methylheptyl, 5-methylheptyl, 6-methylheptyl, 1-ethylhexyl, 2-ethylhexyl, 3-ethylhexyl, 4-ethylhexyl, 1,1-dimethylhexyl, 1,2-dimethylhexyl, 1,3-dimethylhexyl, 1,4-dimethylhexyl, 1,5-dimethylhexyl, n-nonyl, 1-methyloctyl, 2-methyloctyl, 3-methyloctyl, 4-methyloctyl, 5-methyloctyl, 6-methyloctyl, 7-methyloctyl, 1-ethylheptyl, 2-ethylheptyl, 3-ethylheptyl, 4-ethylheptyl, 5-ethylheptyl, 6-ethylheptyl, 1,1-dimethylheptyl, 1,2-dimethylheptyl, 1,3-dimethylheptyl, 1,4-dimethylheptyl, 1,5-dimethylheptyl, 1,6-dimethylheptyl, n-decyl, 1-methylnonyl, 2-methylnonyl, 3-methylnonyl, 7-methylnonyl, 8-methylnonyl, 1-ethyloctyl, 2-ethyloctyl, 3-ethyloctyl, 4-ethyloctyl, 5-ethyloctyl, 6-ethyloctyl, 7-ethyloctyl, 8-ethyloctyl, 1,1-dimethyloctyl, 1,2-dimethyloctyl, 1,3-dimethyloctyl, 1,4-dimethyloctyl, 1,5-dimethyloctyl, 1,6-dimethyloctyl, 1,7-dimethyloctyl, n-undecyl, 1-methyldecyl, 1-ethylnonyl, 1,1-dimethylnonyl, 1-propyloctyl, 1-butylheptyl, 6-undecyl, n-dodecyl, 1-methylundecyl, 1-ethyldecyl, 1,1-dimethyldecyl, 1-propylnonyl, 1-butyloctyl, 7-dodecyl, n-tridecyl, 1-methyldodecyl, 1-ethylundecyl, 1,1-dimethylundecyl, n-tetradecyl, 1-methyltridecyl, 1-ethyldodecyl, 1,1-dimethyldodecyl, n-pentadecyl, 1-methyltetradecyl, 1-ethyltridecyl, 1,1-dimethyltridecyl in particular CH₃, C₂H₅, n-propyl, CH(CH₃)₂, n-butyl, C(CH₃)₃, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl;

C₁-C₄-haloalkyl: a C₁-C₄-alkyl radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e., for example, CH₂F, CHF₂, CF₃, CH₂Cl, dichloromethyl, trichloromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, C₂F₅, 2-fluoropropyl, 3-fluoropropyl, 2,2-difluoropropyl, 2,3-difluoropropyl, 2-chloropropyl, 3-chloropropyl, 2,3-dichloropropyl, 2-bromopropyl, 3-bromopropyl, 3,3,3-trifluoropropyl, 3,3,3-trichloropropyl, 2,2,3,3,3-pentafluoropropyl, heptafluoropropyl, 1-(fluoromethyl)-2-fluoroethyl, 1-(chloromethyl)-2-chloroethyl, 1-(bromomethyl)-2-bromoethyl, 4-fluorobutyl, 4-chlorobutyl, 4-bromobutyl or nonafluorobutyl, in particular CH₂F, CHF₂, CF₃, CH₂Cl, 2-fluoroethyl, 2-chloroethyl or 2,2,2-trifluoroethyl;

C₁-C₆-haloalkyl: C₁-C₆-alkyl as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e., for example, one of the radicals mentioned under C₁-C₄-haloalkyl, or 5-fluoro-1-pentyl, 5-chloro-1-pentyl, 5-bromo-1-pentyl, 5-iodo-1-pentyl, 5,5,5-trichloro-1-pentyl, undecafluoropentyl, 6-fluoro-1-hexyl, 6-chloro-1-hexyl, 6-bromo-1-hexyl, 6-iodo-1-hexyl, 6,6,6-trichloro-1-hexyl or dodecafluorohexyl, in particular chloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, 2-fluoroethyl, 2-chloroethyl or 2,2,2-trifluoroethyl;

hydroxy-C₁-C₆-alkyl: for example hydroxymethyl, 2-hydroxyeth-1-yl, 2-hydroxyprop-1-yl, 3-hydroxyprop-1-yl, 1-hydroxyprop-2-yl, 2-hydroxybut-1-yl, 3-hydroxybut-1-yl, 4-hydroxybut-1-yl, 1-hydroxybut-2-yl, 1-hydroxybut-3-yl, 2-hydroxybut-3-yl, 1-hydroxy-2-methylprop-3- yl, 2-hydroxy-2-methylprop-3-yl or 2-hydroxymethylprop-2-yl, in particular 2-hydroxyethyl;

cyano-C₁-C₆-alkyl: for example cyanomethyl, 1-cyanoeth-1-yl, 2-cyanoeth-1-yl, 1-cyanoprop-1-yl, 2-cyanoprop-1-yl, 3-cyanoprop-1-yl, 1-cyanoprop-2-yl, 2-cyanoprop-2-yl, 1-cyanobut-1-yl, 2-cyanobut-1-yl, 3-cyanobut-1-yl, 4-cyanobut-1-yl, 1-cyanobut-2-yl, 2-cyanobut-2-yl, 1-cyanobut-3-yl, 2-cyanobut-3-yl, 1-cyano-2-methylprop-3-yl, 2-cyano-2-methylprop-3-yl, 3-cyano-2-methylprop-3-yl or 2-cyanomethylprop-2-yl, in particular cyanomethyl or 2-cyanoethyl;

phenyl-C₁-C₆-alkyl: for example benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylprop-1-yl, 2-phenylprop-1-yl, 3-phenylprop-1-yl, 1-phenylbut-1-yl, 2-phenylbut-1-yl, 3-phenylbut-1-yl, 4-phenylbut-1-yl, 1-phenylbut-2-yl, 2-phenylbut-2-yl, 3-phenylbut-2-yl, 4-phenylbut-2-yl, 1-(phenylmethyl) eth-1-yl, 1-(phenylmethyl)-1-(methyl)eth-1-yl or 1-(phenylmethyl)prop-1-yl, in particular benzyl or 2-phenylethyl;

phenyl-(C₁-C₆-alkyl)carbonyloxy: for example benzylcarbonyloxy, 1-phenylethylcarbonyloxy, 2-phenylethylcarbonyloxy, 1-phenylprop-1-ylcarbonyloxy, 2-phenylprop-1-ylcarbonyloxy, 3-phenylprop-1-ylcarbonyloxy, 1-phenylbut-1-ylcarbonyloxy, 2-phenylbut-1-ylcarbonyloxy, 3-phenylbut-1-ylcarbonyloxy, 4-phenylbut-1-ylcarbonyloxy, 1-phenylbut-2-ylcarbonyloxy, 2-phenylbut-2-ylcarbonyloxy, 3-phenylbut-2-ylcarbonyloxy, 4-phenylbut-2-ylcarbonyloxy, 1-(phenylmethyl)eth-1-ylcarbonyloxy, 1-(phenylmethyl)-1-(methyl)eth-1-ylcarbonyloxy or 1-(phenylmethyl)prop-1-ylcarbonyloxy, in particular benzylcarbonyloxy or 2-phenylethylcarbonyloxy;

phenyl-C₁-C₆-alkylsulfonyloxy: for example benzylsulfonyloxy, 1-phenylethylsulfonyloxy, 2-phenylethysulfonyloxy, 1-phenylprop-1-ylsulfonyloxy, 2-phenylprop-1-ylsulfonyloxy, 3-phenylprop-1-ylsulfonyloxy, 1-phenylbut-1-ylsulfonyloxy, 2-phenylbut-1-ylsulfonyloxy, 3-phenylbut-1-ylsulfonyloxy, 4-phenylbut-1-ylsulfonyloxy, 1-phenylbut-2-ylsulfonyloxy, 2-phenylbut-2-ylsulfonyloxy, 3-phenylbut-2-ylsulfonyloxy, 4-phenylbut-2-ylsulfonyloxy, 1-(phenylmethyl)eth-1-ylsulfonyloxy, 1-(phenylmethyl)-1-(methyl)eth-1-ylsulfonyloxy or 1-(phenylmethyl)prop-1-ylsulfonyloxy, in particular benzylsulfonyloxy or 2-phenylethylsulfonyloxy;

(C₁-C₆-alkyl)carbonyl: CO—CH₃, CO—C₂H₅, n-propylcarbonyl, 1-methylethylcarbonyl, n-butylcarbonyl, 1-methylpropylcarbonyl, 2-methylpropylcarbonyl, 1,1-dimethylethylcarbonyl, n-pentylcarbonyl, 1-methylbutylcarbonyl, 2-methylbutylcarbonyl, 3-methylbutylcarbonyl, 1,1-dimethylpropylcarbonyl, 1,2-dimethylpropylcarbonyl, 2,2-dimethylpropylcarbonyl, 1-ethylpropylcarbonyl, n-hexylcarbonyl, 1-methylpentylcarbonyl, 2-methylpentylcarbonyl, 3-methylpentylcarbonyl, 4-methylpentylcarbonyl, 1,1-dimethylbutylcarbonyl, 1,2-dimethylbutylcarbonyl, 1,3-dimethylbutylcarbonyl, 2,2-dimethylbutylcarbonyl, 2,3-dimethylbutylcarbonyl, 3,3-dimethylbutylcarbonyl, 1-ethylbutylcarbonyl, 2-ethylbutylcarbonyl, 1,1,2-trimethylpropylcarbonyl, 1,2,2-trimethylpropylcarbonyl, 1-ethyl-1-methylpropylcarbonyl or 1-ethyl-2-methylpropylcarbonyl, in particular CO—CH₃, CO—C₂H₅ or CO—CH(CH₃)₂;

(C₁-C₆-alkyl)carbonyl-C₁-C₆-alkyl: (C₁-C₆-alkyl) which is substituted by (C₁-C₆-alkyl)carbonyl as mentioned above, i.e., for example, methylcarbonylmethyl;

(C₁-C₆-haloalkyl)carbonyl: a (C₁-C₆-alkyl)carbonyl radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e., for example, chloroacetyl, dichloroacetyl, trichloroacetyl, fluoroacetyl, difluoroacetyl, trifluoroacetyl, chlorofluoroacetyl, dichlorofluoroacetyl, chlorodifluoroacetyl, 2-fluoroethylcarbonyl, 2-chloroethylcarbonyl, 2-bromoethylcarbonyl, 2-iodoethylcarbonyl, 2,2-difluoroethylcarbonyl, 2,2,2-trifluoroethylcarbonyl, 2-chloro-2-fluoroethylcarbonyl, 2-chloro-2,2-difluoroethylcarbonyl, 2,2-dichloro-2-fluoroethylcarbonyl, 2,2,2-trichloroethylcarbonyl, pentafluoroethylcarbonyl, 2-fluoropropylcarbonyl, 3-fluoropropylcarbonyl, 2,2-difluoropropylcarbonyl, 2,3-difluoropropylcarbonyl, 2-chloropropylcarbonyl, 3-chloropropylcarbonyl, 2,3-dichloropropylcarbonyl, 2-bromopropylcarbonyl, 3-bromopropylcarbonyl, 3,3,3-trifluoropropylcarbonyl, 3,3,3-trichloropropylcarbonyl, 2,2,3,3,3-pentafluoropropylcarbonyl, heptafluoropropylcarbonyl, 1-(fluoromethyl)-2-fluoroethylcarbonyl, 1-(chloromethyl)-2-chloroethylcarbonyl, 1-(bromomethyl)-2-bromoethylcarbonyl, 4-fluorobutylcarbonyl, 4-chlorobutylcarbonyl, 4-bromobutylcarbonyl, nonafluorobutylcarbonyl, (5-fluoro-1-pentyl)carbonyl, (5-chloro-1-pentyl)carbonyl, (5-bromo-1-pentyl)carbonyl, (5-iodo-1-pentyl)carbonyl, (5,5,5-trichloro-1-pentyl)carbonyl, undecafluoropentylcarbonyl, (6-fluoro-1-hexyl)carbonyl, (6-chloro-1-hexyl)carbonyl, (6-bromo-1-hexyl)carbonyl, (6-iodo-1-hexyl)carbonyl, (6,6,6-trichloro-1-hexyl)carbonyl or dodecafluorohexylcarbonyl, in particular trifluoroacetyl;

(C₁-C₆-alkyl)carbonyloxy: acetyloxy, ethylcarbonyloxy, n-propylcarbonyloxy, 1-methylethylcarbonyloxy, n-butylcarbonyloxy, 1-methylpropylcarbonyloxy, 2-methylpropylcarbonyloxy, 1,1-dimethylethylcarbonyloxy, n-pentylcarbonyloxy, 1-methylbutylcarbonyloxy, 2-methylbutylcarbonyloxy, 3-methylbutylcarbonyloxy, 1,1-dimethylpropylcarbonyloxy, 1,2-dimethylpropylcarbonyloxy, 2,2-dimethylpropylcarbonyloxy, 1-ethylpropylcarbonyloxy, n-hexylcarbonyloxy, 1-methylpentylcarbonyloxy, 2-methylpentylcarbonyloxy, 3-methylpentylcarbonyloxy, 4-methylpentylcarbonyloxy, 1,1-dimethylbutylcarbonyloxy, 1,2-dimethylbutylcarbonyloxy, 1,3-dimethylbutylcarbonyloxy, 2,2-dimethylbutylcarbonyloxy, 2,3-dimethylbutylcarbonyloxy, 3,3-dimethylbutylcarbonyloxy, 1-ethylbutylcarbonyloxy, 2-ethylbutylcarbonyloxy, 1,1,2-trimethylpropylcarbonyloxy, 1,2,2-trimethylpropylcarbonyloxy, 1-ethyl-1-methylpropylcarbonyloxy or 1-ethyl-2-methylpropylcarbonyloxy, in particular acetyloxy; (C₁-C₆-haloalkyl)carbonyloxy: a (C₁-C₆-alkyl)carbonyloxy radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e., for example, chloroacetyloxy, dichloroacetyloxy, trichloroacetyloxy, fluoroacetyloxy, difluoroacetyloxy, trifluoroacetyloxy, chlorofluoroacetyloxy, dichlorofluoroacetyloxy, chlorodifluoroacetyloxy, 2-fluoroethylcarbonyloxy, 2-chloroethylcarbonyloxy, 2-bromoethylcarbonyloxy, 2-iodoethylcarbonyloxy, 2,2-difbluoroethylcarbonyloxy, 2,2,2-trifluoroethylcarbonyloxy, 2-chloro-2-fluoroethylcarbonyloxy, 2-chloro-2,2-difluoroethylcarbonyloxy, 2,2-dichloro-2-fluoroethylcarbonyloxy, 2,2,2-trichloroethylcarbonyloxy, pentafluoroethylcarbonyloxy, 2-fluoropropylcarbonyloxy, 3-fluoropropylcarbonyloxy, 2,2-difluoropropylcarbonyloxy, 2,3-difluoropropylcarbonyloxy, 2-chloropropylcarbonyloxy, 3-chloropropylcarbonyloxy, 2,3-dichloropropylcarbonyloxy, 2-bromopropylcarbonyloxy, 3-bromopropylcarbonyloxy, 3,3,3-trifluoropropylcarbonyloxy, 3,3,3-trichloropropylcarbonyloxy, 2,2,3,3,3-pentafluoropropylcarbonyloxy, heptafluoropropylcarbonyloxy, 1-(fluoromethyl)-2-fluoroethylcarbonyloxy, 1-(chloromethyl)-2-chloroethylcarbonyloxy, 1-(bromomethyl)-2-bromoethylcarbonyloxy, 4-fluorobutylcarbonyloxy, 4-chlorobutylcarbonyloxy, 4-bromobutyl or nonafluorobutyl, in particular trifluoroacetoxy;

(C₁-C₆-alkyl)carbonyloxy-C₁-C₆-alkyl: (C₁-C₆-alkyl) which is substituted by (C₁-C₆-alkyl)carbonyloxy as mentioned above, i.e., for example, methylcarbonyloxymethyl, ethylcarbonyloxymethyl, 1-(methylcarbonyloxy)ethyl, 2-(methylcarbonyloxy)ethyl, 2-(ethylcarbonyloxy)ethyl, 3-(methylcarbonyloxy) propyl, 4-(methoxycarbonyloxy) butyl, 5-(methoxycarbonyloxy)pentyl or 6-(methoxycarbonyloxy)hexyl;

(C₁-C₆-alkyl)carbonylthio: acetylthio, ethylcarbonylthio, n-propylcarbonylthio, 1-methylethylcarbonylthio, n-butylcarbonylthio, 1-methylpropylcarbonylthio, 2-methylpropylcarbonylthio, 1,1-dimethylethylcarbonylthio, n-pentylcarbonylthio, 1-methylbutylcarbonylthio, 2-methylbutylcarbonylthio, 3-methylbutylcarbonylthio, 1,1-dimethylpropylcarbonylthio, 1,2-dimethylpropylcarbonylthio, 2,2-dimethylpropylcarbonylthio, 1-ethylpropylcarbonylthio, n-hexylcarbonylthio, 1-methylpentylcarbonylthio, 2-methylpentylcarbonylthio, 3-methylpentylcarbonylthio, 4-methylpentylcarbonylthio, 1,1-dimethylbutylcarbonylthio, 1,2-dimethylbutylcarbonylthio, 1,3-dimethylbutylcarbonylthio, 2,2-dimethylbutylcarbonylthio, 2,3-dimethylbutylcarbonylthio, 3,3-dimethylbutylcarbonylthio, 1-ethylbutyicarbonylthio, 2-ethylbutylcarbonylthio, 1,1,2-trimethylpropylcarbonylthio, 1,2,2-trimethylpropylcarbonylthio, 1-ethyl-1-methylpropylcarbonylthio or 1-ethyl-2-methylpropylcarbonylthio, in particular acetylthio;

(C₁-C₆-haloalkyl)carbonylthio: a (C₁-C₆-alkyl)carbonylthio radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e., for example, chloroacetylthio, dichloroacetylthio, trichloroacetylthio, fluoroacetylthio, difluoroacetylthio, trifluoroacetylthio, chlorofluoroacetylthio, dichlorofluoroacetylthio, chlorodifluoroacetylthio, 2-fluoroethylcarbonylthio, 2-chloroethylcarbonylthio, 2-bromoethylcarbonylthio, 2-iodoethylcarbonylthio, 2,2-difluoroethylcarbonylthio, 2,2,2-trifluoroethylcarbonylthio, 2-chloro-2-fluoroethylcarbonylthio, 2-chloro-2,2-difluoroethylcarbonylthio, 2,2-dichloro-2-fluoroethylcarbonylthio, 2,2,2-trichloroethylcarbonylthio, pentafluoroethylcarbonylthio, 2-fluoropropylcarbonylthio, 3-fluoropropylcarbonylthio, 2,2-difluoropropylcarbonylthio, 2,3-difluoropropylcarbonylthio, 2-chloropropylcarbonylthio, 3-chloropropylcarbonylthio, 2,3-dichloropropylcarbonylthio, 2-bromopropylcarbonylthio, 3-bromopropylcarbonylthio, 3,3,3-trifluoropropylcarbonylthio, 3,3,3-trichloropropylcarbonylthio, 2,2,3,3,3-pentafluoropropylcarbonylthio, heptafluoropropylcarbonylthio, 1-(fluoromethyl)-2-fluoroethylcarbonylthio, 1-(chloromethyl)-2-chloroethylcarbonylthio, 1-(bromomethyl)-2-bromoethylcarbonylthio, 4-fluorobutylcarbonylthio, 4-chlorobutylcarbonylthio, 4-bromobutylthio or nonafluorobutylthio, in particular trifluoroacetylthio;

(C₁-C₆-alkyl)carbamoyloxy: methylcarbamoyloxy, ethylcarbamoyloxy, n-propylcarbamoyloxy, 1-methylethylcarbamoyloxy, n-butylcarbamoyloxy, 1-methylpropylcarbamoyloxy, 2-methylpropylcarbamoyloxy, 1,1-dimethylethylcarbamoyloxy, n-pentylcarbamoyloxy, 1-methylbutylcarbamoyloxy, 2-methylbutylcarbamoyloxy, 3-methylbutylcarbamoyloxy, 1,1-dimethylpropylcarbamoyloxy, 1,2-dimethylpropylcarbamoyloxy, 2,2-dimethylpropylcarbamoyloxy, 1-ethylpropylcarbamoyloxy, n-hexylcarbamoyloxy, 1-methylpentylcarbamoyloxy, 2-methylpentylcarbamoyloxy, 3-methylpentylcarbamoyloxy, 4-methylpentylcarbamoyloxy, 1,1-dimethylbutylcarbamoyloxy, 1,2-dimethylbutylcarbamoyloxy, 1,3-dimethylbutylcarbamoyloxy, 2,2-dimethylbutylcarbamoyloxy, 2,3-dimethylbutylcarbamoyloxy, 3,3-dimethylbutylcarbamoyloxy, 1-ethylbutylcarbamoyloxy, 2-ethylbutylcarbamoyloxy, 1,1,2-trimethylpropylcarbamoyloxy, 1,2,2-trimethylpropylcarbamoyloxy, 1-ethyl-1-methylpropylcarbamoyloxy or 1-ethyl-2-methylpropylcarbamoyloxy, in particular methylcarbamoyloxy;

(C₁-C₆-haloalkyl)carbamoyloxy: a (C₁-C₆-alkyl)carbamoyloxy radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e., for example, chloromethylcarbamoyloxy, dichloromethylcarbamoyloxy, trichloromethylcarbamoyloxy, fluoromethylcarbamoyloxy, difluoromethylcarbamoyloxy, trifluoromethylcarbamoyloxy, chlorofluoromethylcarbamoyloxy, dichlorofluoromethylcarbamoyloxy, chlorodifluoromethylcarbamoyloxy, 2-fluoroethylcarbamoyloxy, 2-chloroethylcarbamoyloxy, 2-bromoethylcarbamoyloxy, 2-iodoethylcarbamoyloxy, 2,2-difluoroethylcarbamoyloxy, 2,2,2-trifluoroethylcarbamoyloxy, 2-chloro-2-fluoroethylcarbamoyloxy, 2-chloro-2,2-difluoroethylcarbamoyloxy, 2,2-dichloro-2-fluoroethylcarbamoyloxy, 2,2,2-trichloroethylcarbamoyloxy, pentafluoroethylcarbamoyloxy, 2-fluoropropylcarbamoyloxy, 3-fluoropropylcarbamoyloxy, 2,2-difluoropropylcarbamoyloxy,. 2,3-difluoropropylcarbamoyloxy, 2-chloropropylcarbamoyloxy, 3-chloropropylcarbamoyloxy, 2,3-dichloropropylcarbamoyloxy, 2-bromopropylcarbamoyloxy, 3-bromopropylcarbamoyloxy, 3,3,3-trifluoropropylcarbamoyloxy, 3,3,3-trichloropropylcarbamoyloxy, 2,2,3,3,3-pentafluoropropylcarbamoyloxy, heptafluoropropylcarbamoyloxy, 1-(fluoromethyl)-2-fluoroethylcarbamoyloxy, 1-(chloromethyl)-2-chloroethylcarbamoyloxy, 1-(bromomethyl)-2-bromoethylcarbamoyloxy, 4-fluorobutylcarbamoyloxy, 4-chlorobutylcarbamoyloxy, 4-bromobutylcarbamoyloxy or nonafluorobutylcarbamoyloxy, in particular trifluoromethylcarbamoyloxy;

C₁-C₆-alkoxy: for example OCH₃, OC₂H₅, OCH₂—C₂H₅, OCH(CH₃)₂, n-butoxy, OCH(CH₃)—C₂H₅, OCH₂—CH(CH₃)₂, OC(CH₃)₃, n-pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, n-hexoxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 2-ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy and 1-ethyl-2-methylpropoxy, in particular OCH₃, OC₂H₅ or OCH(CH₃)₂;

C₁-C₄-haloalkoxy: a C₁-C₄-alkoxy radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e., for example, chloromethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, pentafluoroethoxy, 2-fluoropropoxy, 3-fluoropropoxy, 2,2-difluoropropoxy, 2,3-difluoropropoxy, 2-chloropropoxy, 3-chloropropoxy, 2,3-dichloropropoxy, 2-bromopropoxy, 3-bromopropoxy, 3,3,3-trifluoropropoxy, 3,3,3-trichloropropoxy, 2,2,3,3,3-pentafluoropropoxy, heptafluoropropoxy, 1-(fluoromethyl)-2-fluoroethoxy, 1-(chloromethyl)-2-chloroethoxy, 1-(bromomethyl)-2-bromoethoxy, 4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy or nonafluorobutoxy, in particular 2-chloroethoxy or 2,2,2-trifluoroethoxy;

C₁-C₆-haloalkoxy: a C₁-C₆-alkoxy radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e., for example, one of the radicals mentioned under C₁-C₄-haloalkoxy, or 5-fluoro-1-pentoxy, 5-chloro-1-pentoxy, 5-bromo-1-pentoxy, 5-iodo-1-pentoxy, 5,5,5-trichloro-1-pentoxy, undecafluoropentoxy, 6-fluoro-1-hexoxy, 6-chloro-1-hexoxy, 6-bromo-1-hexoxy, 6-iodo-1-hexoxy, 6,6,6-trichloro-1-hexoxy or dodecafluorohexoxy, in particular chloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy or 2,2,2-trifluoroethoxy;

hydroxy-C₁-C₆-alkoxy: for example OCH₂—OH, OCH(CH₃)—OH, OCH₂—CH₂—OH, OCH(C₂H₅)—OH, OCH₂—CH(CH₃)—OH, 3-hydroxyprop-1-yloxy, 1-hydroxybut-1-yloxy, 2-hydroxybut-1-yloxy, 3-hydroxybut-1-yloxy, 4-hydroxybut-1-yloxy, 1-hydroxybut-2-yloxy, 2-hydroxybut-2-yloxy, 3-hydroxybut-2-yloxy, 4-hydroxybut-2-yloxy, 1-(CH₂—OH)-eth-1-yloxy, 1-(CH₂—OH)-1-(CH₃)-eth-1-yloxy or 1-(CH₂—OH)-prop-1-yloxy, in particular OCH₂—OH or OCH₂—CH₂—OH;

cyano-C₁-C₆-alkoxy: for example OCH₂—CN, OCH(CH₃)—CN, OCH₂—CH₂—CN, OCH(C₂H₅)—OH, OCH₂—CH(CH₃)—CN, 3-cyanoprop-1-yloxy, 1-cyanobut-1-yloxy, 2-cyanobut-1-yloxy, 3-cyanobut-1-yloxy, 4-cyanobut-1-yloxy, 1-cyanobut-2-yloxy, 2-cyanobut-2-yloxy, 3-cyanobut-2-yloxy, 4-cyanobut-2-yloxy, 1-(CH₂—CN)-eth-1-yloxy, 1-(CH₂—CN)-1-(CH₃)-eth-1-yloxy or 1-(CH₂—CN)-prop-1-yloxy, in particular OCH₂—CN or OCH₂—CH₂—CN;

phenyl-C₁-C₆-alkoxy: for example benzyloxy, 1-phenylethoxy, 2-phenylethoxy, 1-phenylprop-1-yloxy, 2-phenylprop-1-yloxy, 3-phenylprop-1-yloxy, 1-phenylbut-1-yloxy, 2-phenylbut-1-yloxy, 3-phenylbut-1-yloxy, 4-phenylbut-1-yloxy, 1-phenylbut-2-yloxy, 2-phenylbut-2-yloxy, 3-phenylbut-2-yloxy, 4-phenylbut-2-yloxy, 1-(benzyl)eth-1-yloxy, 1-(benzyl)-1-(methyl)eth-1-yloxy or 1-(benzyl)prop-1-yloxy, in particular benzyloxy or 2-phenylethoxy;

phenyl-C₁-C₆-alkylthio: for example benzylthio, 1-phenylethylthio, 2-phenylethylthio, 1-phenylprop-1-ylthio, 2-phenylprop-1-ylthio, 3-phenylprop-1-ylthio, 1-phenylbut-1-ylthio, 2-phenylbut-1-ylthio, 3-phenylbut-1-ylthio, 4-phenylbut-1-ylthio, 1-phenylbut-2-ylthio, 2-phenylbut-2-ylthio, 3-phenylbut-2-ylthio, 4-phenylbut-2-ylthio, 1-(phenylmethyl)eth-1-ylthio, 1-(phenylmethyl)-1-(methyl)eth-1-ylthio or 1-(phenylmethyl)prop-1-ylthio, in particular benzylthio or 2-phenylethylthio;

(C₁-C₆-alkoxy)carbonyl: for example CO—OCH₃, CO—OC₂H₅, CO—CH₂—C₂H₅, CO—OCH(CH₃)₂, n-butoxycarbonyl, CO—OCH(CH₃)—C₂H₅, CO—OCH₂—CH(CH₃)₂, CO—OC(CH₃)₃, n-pentoxycarbonyl, 1-methylbutoxycarbonyl, 2-methylbutoxycarbonyl, 3-methylbutoxycarbonyl, 2,2-dimethylpropoxycarbonyl, 1-ethylpropoxycarbonyl, n-hexoxycarbonyl, 1,1-dimethylpropoxycarbonyl, 1,2-dimethylpropoxycarbonyl, 1-methylpentoxycarbonyl, 2-methylpentoxycarbonyl, 3-methylpentoxycarbonyl, 4-methylpentoxycarbonyl, 1,1-dimethylbutoxycarbonyl, 1,2-dimethylbutoxycarbonyl, 1,3-dimethylbutoxycarbonyl, 2,2-dimethylbutoxycarbonyl, 2,3-dimethylbutoxycarbonyl, 3,3-dimethylbutoxycarbonyl, 1-ethylbutoxycarbonyl, 2-ethylbutoxycarbonyl, 1,1,2-trimethylpropoxycarbonyl, 1,2,2-trimethylpropoxycarbonyl, 1-ethyl-1-methylpropoxycarbonyl or 1-ethyl-2-methylpropoxycarbonyl, in particular CO—OCH₃, CO—OC₂H₅, CO—OCH(CH₃)₂ or CO—CH₂—CH(CH₃)₂;

(C₁-C₆-alkoxy)carbonyloxy: methoxycarbonyloxy, ethoxycarbonyloxy, n-propoxycarbonyloxy, 1-methylethoxycarbonyloxy, n-butoxycarbonyloxy, 1-methylpropoxycarbonyloxy, 2-methylpropoxycarbonyloxy, 1,1-dimethylethoxycarbonyloxy, n-pentoxycarbonyloxy, 1-methylbutoxycarbonyloxy, 2-methylbutoxycarbonyloxy, 3-methylbutoxycarbonyloxy, 2,2-dimethylpropoxycarbonyloxy, 1-ethylpropoxycarbonyloxy, n-hexoxycarbonyloxy, 1,1-dimethylpropoxycarbonyloxy, 1,2-dimethylpropoxycarbonyloxy, 1-methylpentoxycarbonyloxy, 2-methylpentoxycarbonyloxy, 3-methylpentoxycarbonyloxy, 4-methylpentoxycarbonyloxy, 1,1-dimethylbutoxycarbonyloxy, 1,2-dimethylbutoxycarbonyloxy, 1,3-dimethylbutoxycarbonyloxy, 2,2-dimethylbutoxycarbonyloxy, 2,3-dimethylbutoxycarbonyloxy, 3,3-dimethylbutoxycarbonyloxy, 1-ethylbutoxycarbonyloxy, 2-ethylbutoxycarbonyloxy, 1,1,2-trimethylpropoxycarbonyloxy, 1,2,2-trimethylpropoxycarbonyloxy, 1-ethyl-1-methylpropoxycarbonyloxy or 1-ethyl-2-methylpropoxycarbonyloxy, in particular methoxycarbonyloxy, ethoxycarbonyloxy or 1-methylethoxycarbonyloxy;

(C₁-C₆-alkoxy)carbonylthio: methoxycarbonylthio, ethoxycarbonylthio, n-propoxycarbonylthio, 1-methylethoxycarbonylthio, n-butoxycarbonylthio, 1-methylpropoxycarbonylthio, 2-methylpropoxycarbonylthio, 1,1-dimethylethoxycarbonylthio, n-pentoxycarbonylthio, 1-methylbutoxycarbonylthio, 2-methylbutoxycarbonylthio, 3-methylbutoxycarbonylthio, 2,2-dimethylpropoxycarbonylthio, 1-ethylpropoxycarbonylthio, n-hexoxycarbonylthio, 1,1-dimethylpropoxycarbonylthio, 1,2-dimethylpropoxycarbonylthio, 1-methylpentoxycarbonylthio, 2-methylpentoxycarbonylthio, 3-methylpentoxycarbonylthio, 4-methylpentoxycarbonylthio, 1,1-dimethylbutoxycarbonylthio, 1,2-dimethylbutoxycarbonylthio, 1,3-dimethylbutoxycarbonylthio, 2,2-dimethylbutoxycarbonylthio, 2,3-dimethylbutoxycarbonylthio, 3,3-dimethylbutoxycarbonylthio, 1-ethylbutoxycarbonylthio, 2-ethylbutoxycarbonylthio, 1,1,2-trimethylpropoxycarbonylthio, 1,2,2-trimethylpropoxycarbonylthio, 1-ethyl-1-methylpropoxycarbonylthio or 1-ethyl-2-methylpropoxycarbonylthio, in particular methoxycarbonylthio, ethoxycarbonylthio or 1-methylethoxycarbonylthio;

C₁-C₆-alkylthio: SCH₃, SC₂H₅, SCH₂—C₂H₅, SCH(CH₃)₂, n-butylthio, 1-methylpropylthio, 2-methylpropylthio, SC(CH₃)₃, n-pentylthio, 1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, 2,2-dimethylpropylthio, 1-ethylpropylthio, n-hexylthio, 1,1-dimethylpropylthio, 1,2-dimethylpropylthio, 1-methylpentylthio, 2-methylpentylthio, 3-methylpentylthio, 4-methylpentylthio, 1,1-dimethylbutylthio, 1,2-dimethylbutylthio, 1,3-dimethylbutylthio, 2,2-dimethylbutylthio, 2,3-dimethylbutylthio, 3,3-dimethylbutylthio, 1-ethylbutylthio, 2-ethylbutylthio, 1,1,2-trimethylpropylthio, 1,2,2-trimethylpropylthio, 1-ethyl-1-methylpropylthio and 1-ethyl-2-methylpropylthio, in particular SCH₃ or SC₂H₅;

C₁-C₆-haloalkylthio: C₁-C₆-alkylthio as mentioned above, which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e., for example, SCHF₂, SCF₃, chlorodifluoromethylthio, bromodifluoromethylthio, 2-fluoroethylthio, 2-chloroethylthio, 2-bromoethylthio, 2-iodoethylthio, 2,2-difluoroethylthio, 2,2,2-trifluoroethylthio, 2,2,2-trichloroethylthio, 2-chloro-2-fluoroethylthio, 2-chloro-2,2-difluoroethylthio, 2,2-dichloro-2-fluoroethylthio, SC₂F₅, 2-fluoropropylthio, 3-fluoropropylthio, 2-chloropropylthio, 3-chloropropylthio, 2-bromopropylthio, 3-bromopropylthio, 2,2-difluoropropylthio, 2,3-difluoropropylthio, 2,3-dichloropropylthio, 3,3,3-trifluoropropylthio, 3,3,3-trichloropropylthio, 2,2,3,3,3-pentafluoropropylthio, heptafluoropropylthio, 1-(fluoromethyl)-2-fluoroethylthio, 1-(chloromethyl)-2-chloroethylthio, 1-(bromomethyl)-2-bromoethylthio, 4-fluorobutylthio, 4-chlorobutylthio, 4-bromobutylthio, nonafluorobutylthio, 5-fluoropentylthio, 5-chloropentylthio, 5-bromopentylthio, 5-iodopentylthio, undecafluoropentylthio, 6-fluorohexylthio or 6-chlorohexylthio, in particular SCH₂F, SCHF₂, SCF₃, SCH₂Cl, 2-fluoroethylthio, 2-chloroethylthio or 2,2,2-trifluoroethylthio;

C₁-C₆-alkylsulfinyl: SO—CH₃, SO—C₂H₅, n-propylsulfinyl, 1-methylethylsulfinyl, n-butylsulfinyl, 1-methylpropylsulfinyl, 2-methylpropylsulfinyl, 1,1-dimethylethylsulfinyl, n-pentylsulfinyl, 1-methylbutylsulfinyl, 2-methylbutylsulfinyl, 3-methylbutylsulfinyl, 1,1-dimethylpropylsulfinyl, 1,2-dimethylpropylsulfinyl, 2,2-dimethylpropylsulfinyl, 1-ethylpropylsulfinyl, n-hexylsulfinyl, 1-methylpentylsulfinyl, 2-methylpentylsulfinyl, 3-methylpentylsulfinyl, 4-methylpentylsulfinyl, 1,1-dimethylbutylsulfinyl, 1,2-dimethylbutylsulfinyl, 1,3-dimethylbutylsulfinyl, 2,2-dimethylbutylsulfinyl, 2,3-dimethylbutylsulfinyl, 3,3-dimethylbutylsulfinyl, 1-ethylbutylsulfinyl, 2-ethylbutylsulfinyl, 1,1,2-trimethylpropylsulfinyl, 1,2,2-trimethylpropylsulfinyl, 1-ethyl-1-methylpropylsulfinyl or 1-ethyl-2-methylpropylsulfinyl, in particular SO—CH₃;

C₁-C₆-alkylsulfonyl: SO₂—CH₃, SO₂—C₂H₅, n-propylsulfonyl, SO₂—CH(CH₃)₂, n-butylsulfonyl, 1-methylpropylsulfonyl, 2-methylpropylsulfonyl, SO₂—C(CH₃)₃, n-pentylsulfonyl, 1-methylbutylsulfonyl, 2-methylbutylsulfonyl, 3-methylbutylsulfonyl, 1,1-dimethylpropylsulfonyl, 1,2-dimethylpropylsulfonyl, 2,2-dimethylpropylsulfonyl, 1-ethylpropylsulfonyl, n-hexylsulfonyl, 1-methylpentylsulfonyl, 2-methylpentylsulfbnyl, 3-methylpentylsulfonyl, 4-methylpentylsulfonyl, 1,1-dimethylbutylsulfonyl, 1,2-dimethylbutylsulfonyl, 1,3-dimethylbutylsulfonyl, 2,2-dimethylbutylsulfonyl, 2,3-dimethylbutylsulfonyl, 3,3-dimethylbutylsulfonyl, 1-ethylbutylsulfonyl, 2-ethylbutylsulfonyl, 1,1,2-trimethylpropylsulfonyl, 1,2,2-trimethylpropylsulfonyl, 1-ethyl-1-methylpropylsulfonyl or 1-ethyl-2-methylpropylsulfonyl, in particular SO₂—CH₃;

C₁-C₆-alkylsulfonyloxy: O—SO₂—CH₃, O—SO₂—C₂H₅, n-propylsulfonyloxy, O—SO₂—CH(CH₃)₂, n-butylsulfonyloxy, 1-methylpropylsulfonyloxy, 2-methylpropylsulfonyloxy, O—SO₂—C(CH₃)₃, n-pentylsulfonyloxy, 1-methylbutylsulfonyloxy, 2-methylbutylsulfonyloxy, 3-methylbutylsulfonyloxy, 1,1-dimethylpropylsulfonyloxy, 1,2-dimethylpropylsulfonyloxy, 2,2-dimethylpropylsulfonyloxy, 1-ethylpropylsulfonyloxy,. n-hexylsulfonyloxy, 1-methylpentylsulfonyloxy, 2-methylpentylsulfonyloxy, 3-methylpentylsulfonyloxy, 4-methylpentylsulfonyloxy, 1,1-dimethylbutylsulfonyloxy, 1,2-dimethylbutylsulfonyloxy, 1,3-dimethylbutylsulfonyloxy, 2,2-dimethylbutylsulfonyloxy, 2,3-dimethylbutylsulfonyloxy, 3,3-dimethylbutylsulfonyloxy, 1-ethylbutylsulfonyloxy, 2-ethylbutylsulfonyloxy, 1,1,2-trimethylpropylsulfonyloxy, 1,2,2-trimethylpropylsulfonyloxy, 1-ethyl-1-methylpropylsulfonyloxy or 1-ethyl-2-methylpropylsulfonyloxy, in particular methylsulfonyloxy;

C₁-C₆-haloalkylsulfonyloxy: C₁-C₆-alkylsulfonyloxy as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e., for example, ClCH₂—SO₂—O—, CH(Cl)₂—SO₂—O—, C(Cl)₃—SO₂—O—, FCH₂—SO₂—O—, CHF₂—SO₂—O—, CF₃—SO₂—O—, chlorofluoromethyl-SO₂—O—, dichlorofluoromethyl-SO₂—O—, chlorodifluoromethyl-SO₂—O—, 1-fluoroethyl-SO₂—O—, 2-fluoroethyl-SO₂—O—, 2-chloroethyl-SO₂—O—, 2-bromoethyl-SO₂—O—, 2-iodoethyl-SO₂—O—, 2,2-difluoroethyl-SO₂—O—, 2,2,2-trifluoroethyl-SO₂—O—, 2-chloro-2-fluoroethyl-SO₂—O—, 2-chloro-2,2-difluoroethyl-SO₂—O—, 2,2-dichloro-2-fluoroethyl-SO₂—O—, 2,2,2-trichloroethyl-SO₂—O—, C₂F₅—SO₂—O—, 2-fluoropropyl-SO₂—O—, 3-fluoropropyl-SO₂—O—, 2,2-difluoropropyl-SO₂—O—, 2,3-difluoropropyl-SO₂—O—, 2-chloropropyl-SO₂—O—, 3-chloropropyl-SO₂—O—, 2,3-dichloropropyl-SO₂—O—, 2-bromopropyl-SO₂—O—, 3-bromopropyl-SO₂—O—, 3,3,3-trifluoropropyl-SO₂—O—, 3,3,3-trichloropropyl-SO₂—O—, 2,2,3,3,3-pentafluoropropyl-SO₂—O—, C₂F₅—CF₂—SO₂—O—, 1-(fluoromethyl)-2-fluoroethyl-SO₂—O—, 1-(chloromethyl)-2-chloroethyl-SO₂—O—, 1-(bromomethyl)-2-bromoethyl-SO₂—O—, 4-fluorobutyl-SO₂—O—, 4-chlorobutyl-SO₂—O—, 4-bromobutyl-SO₂—O—, C₂F₅—CF₂—CF₂—SO₂—O—, 5-fluoropentyl-SO₂—O—, 5-chloropentyl-SO₂—O—, 5-bromopentyl-SO₂—O—, 5-iodopentyl-SO₂—O—, 5,5,5-trichloropentyl-SO₂—O—, C₂F₅—CF₂—CF₂—CF₂—SO₂—O—, 6-fluorohexyl-SO₂—O—, 6-chlorohexyl-SO₂—O—, 6-bromohexyl-SO₂—O—, 6-iodohexyl-SO₂—O—, 6,6,6-trichlorohexyl-SO₂—O—or dodecafluorohexyl-SO₂—O—, in particular CF₃—SO₂—O—;

(C₁-C₆-alkyl)aminocarbonyl: (C₁-C₄-alkyl)aminocarbonyl as mentioned above and also for example, n-pentylaminocarbonyl, 1-methylbutylaminocarbonyl, 2-methylbutylaminocarbonyl, 3-methylbutylaminocarbonyl, 2,2-dimethylpropylaminocarbonyl, 1-ethylpropylaminocarbonyl, n-hexylaminocarbonyl, 1,1-dimethylpropylaminocarbonyl, 1,2-dimethylpropylaminocarbonyl, 1-methylpentylaminocarbonyl, 2-methylpentylaminocarbonyl, 3-methylpentylaminocarbonyl, 4-methylpentylaminocarbonyl, 1,1-dimethylbutylaminocarbonyl, 1,2-dimethylbutylaminocarbonyl, 1,3-dimethylbutylaminocarbonyl, 2,2-dimethylbutylaminocarbonyl, 2,3-dimethylbutylaminocarbonyl, 3,3-dimethylbutylaminocarbonyl, 1-ethylbutylaminocarbonyl, 2-ethylbutylaminocarbonyl, 1,1,2-trimethylpropylaminocarbonyl, 1,2,2-trimethylpropylaminocarbonyl, 1-ethyl-1-methylpropylaminocarbonyl or 1-ethyl-2-methylpropylaminocarbonyl, in particular CO—NH-CH₃, CO—NH—C₂H₅ or CO—NH—CH(CH₃)₂;

di(C₁-C₆-alkyl)aminocarbonyl: for example N,N-dimethylaminocarbonyl, N,N-diethylaminocarbonyl, N,N-dipropylaminocarbonyl, N,N-di(1-methylethyl)aminocarbonyl, N,N-dibutylaminocarbonyl, N,N-di(1-methylpropyl)aminocarbonyl, N,N-di(2-methylpropyl)aminocarbonyl, N,N-di(1,1-dimethylethyl)aminocarbonyl, N-ethyl-N-methylaminocarbonyl, N-methyl-N-propylaminocarbonyl, N-methyl-N-(1-methylethyl)aminocarbonyl, N-butyl-N-methylaminocarbonyl, N-methyl-N-(1-methylpropyl)aminocarbonyl, N-methyl-N-(2-methylpropyl)aminocarbonyl, N-(1,1-dimethylethyl)-N-methylaminocarbonyl, N-ethyl-N-propylaminocarbonyl, N-ethyl-N-(1-methylethyl)aminocarbonyl, N-butyl-N-ethylaminocarbonyl, N-ethyl-N-(1-methylpropyl)aminocarbonyl, N-ethyl-N-(2-methylpropyl)aminocarbonyl, N-ethyl-N-(1,1-dimethylethyl)aminocarbonyl, N-(1-methylethyl)-N-propylaminocarbonyl, N-butyl-N-propylaminocarbonyl, N-(1-methylpropyl)-N-propylaminocarbonyl, N-(2-methylpropyl)-N-propylaminocarbonyl, N-(1,1-dimethylethyl)-N-propylaminocarbonyl, N-butyl-N-(1-methylethyl)aminocarbonyl, N-(1-methylethyl)-N-(1-methylpropyl)aminocarbonyl, N-(1-methylethyl)-N-(2-methylpropyl)aminocarbonyl, N-(1,1-dimethylethyl)-N-(1-methylethyl)aminocarbonyl, N-butyl-N-(1-methylpropyl)aminocarbonyl, N-butyl-N-(2-methylpropyl)aminocarbonyl, N-butyl-N-(1,1-dimethylethyl)aminocarbonyl, N-(1-methylpropyl)-N-(2-methylpropyl)aminocarbonyl, N-(1,1-dimethylethyl)-N-(1-methylpropyl)aminocarbonyl or N-(1,1-dimethylethyl)-N-(2-methylpropyl)aminocarbonyl, in particular N,N-dimethylaminocarbonyl or N,N-diethylaminocarbonyl;

(C₁-C₆-alkyl)iminooxycarbonyl: methyliminooxycarbonyl, ethyliminooxycarbonyl, n-propyliminooxycarbonyl, 1-methylethyliminooxycarbonyl, n-butyliminooxycarbonyl, 1-methylpropyliminooxycarbonyl, 2-methylpropyliminooxycarbonyl, 1,1-dimethylethyliminooxycarbonyl, n-pentyliminooxycarbonyl, 1-methylbutyliminooxycarbonyl, 2-methylbutyliminooxycarbonyl, 3-methylbutyliminooxycarbonyl, 1,1-dimethylpropyliminooxycarbonyl, 1,2-dimethylpropyliminooxycarbonyl, 2,2-dimethylpropyliminooxycarbonyl, 1-ethylpropyliminooxycarbonyl, n-hexyliminooxycarbonyl, 1-methylpentyliminooxycarbonyl, 2-methylpentyliminooxycarbonyl, 3-methylpentyliminooxycarbonyl, 4-methylpentyliminooxycarbonyl, 1,1-dimethylbutyliminooxycarbonyl, 1,2-dimethylbutyliminooxycarbonyl, 1,3-dimethylbutyliminooxycarbonyl, 2,2-dimethylbutyliminooxycarbonyl, 2,3-dimethylbutyliminooxycarbonyl, 3,3-dimethylbutyliminooxycarbonyl, 1-ethylbutyliminooxycarbonyl, 2-ethylbutyliminooxycarbonyl, 1,1,2-trimethylpropyliminooxycarbonyl, 1,2,2-trimethylpropyliminooxycarbonyl, 1-ethyl-1-methylpropyliminooxycarbonyl or 1-ethyl-2-methylpropyliminooxycarbonyl, in particular methyliminooxycarbonyl, ethyliminooxycarbonyl or 1-methylethyliminooxycarbonyl;

C₁-C₆-alkylideneaminoxy: acetylideneaminoxy, 1-propylideneaminoxy, 2-propylideneaminoxy, 1-butylideneaminoxy, 2-butylideneaminoxy or 2-hexylideneaminoxy, in particular acetylideneaminoxy or 2-propylideneaminoxy;

C₁-C₆-alkyliminooxy: methyliminooxy, ethyliminooxy, n-propyliminooxy, 1-methylethyliminooxy, n-butyliminooxy, 1-methylpropyliminooxy, 2-methylpropyliminooxy, n-pentyliminooxy, n-hexyliminooxy, 1-methylpentyliminooxy, 2-methylpentyliminooxy, 3-methylpentyliminooxy or 4-methylpentyliminooxy, in particular methyliminooxy, ethyliminooxy or 1-methylethyliminooxy;

C₁-C₆-alkoxy-(C₁-C₆-alkyl)aminocarbonyl: (C₁-C₆-alkyl)aminocarbonyl such as CO—NH—CH₃, CO—NH—C₂H₅, CO—NH—CH₂—C₂H₅, CO—NH—CH(CH₃)₂, CO—NH—(CH₂)₃-CH₃, CO—NH—CH(CH₃)—C₂H₅, CO—NH—CH₂—CH(CH₃)₂, CO—NH—C(CH₃)₃, CO—NH—(CH₂)₄—CH₃, 1-methylbutylaminocarbonyl, 2-methylbutylaminocarbonyl, 3-methylbutylaminocarbonyl, 2,2-dimethylpropylaminocarbonyl, 1-ethylpropylaminocarbonyl, n-hexylaminocarbonyl, 1,1-dimethylpropylaminocarbonyl, 1,2-dimethylpropylaminocarbonyl, 1-methylpentylaminocarbonyl, 2-methylpentylaminocarbonyl, 3-methylpentylaminocarbonyl, 4-methylpentylaminocarbonyl, 1,1-dimethylbutylaminocarbonyl, 1,2-dimethylbutylaminocarbonyl, 1,3-dimethylbutylaminocarbonyl, 2,2-dimethylbutylaminocarbonyl, 2,3-dimethylbutylaminocarbonyl, 3,3-dimethylbutylaminocarbonyl, 1-ethylbutylaminocarbonyl, 2-ethylbutylaminocarbonyl, 1,1,2-trimethylpropylaminocarbonyl, 1,2,2-trimethylpropylaminocarbonyl, 1-ethyl-1-methylpropylaminocarbonyl and 1-ethyl-2-methylpropylaminocarbonyl, preferably (C₁-C₄-alkyl)aminocarbonyl, which is substituted by C₁-C₆-alkoxy as mentioned above, i.e., for example, CO—NH—CH₂—OCH₃ or CO—NH—CH₂—OC₂H₅; C₁-C₆-alkoxyamino-C₁-C₆-alkyl: for example CH₂—NH—OCH₃, CH₂—NH—OC₂H₅, CH₂—NH—OCH₂—C₂H₅, CH₂—NH—OCH(CH₃)₂, CH₂—NH—OCH₂—CH₂—C₂H₅, CH₂—NH—OCH(CH₃)—C₂H₅, CH₂—NH—OCH₂—CH(CH₃)₂, CH₂—NH—OC(CH₃)₃, CH₂—NH—OCH₂—(CH₂)₃—CH₃, (1-methylbutoxyamino)methyl, (2-methylbutoxyamino)methyl, (3-methylbutoxyamino)methyl, (2,2-dimethylpropoxyamino)methyl, (1-ethylpropoxyamino)methyl, n-hexoxyamino-methyl, (1,1-dimethylpropoxyamino)methyl, (1,2-dimethylpropoxyamino)methyl, (1-methylpentoxyamino)m ethyl, (2-methylpentoxyamino)methyl, (3-methylpentoxyamino)methyl, (4-methylpentoxyamino)methyl, (1,1-dimethylbutoxyamino)methyl, (1,2-dimethylbutoxyamino)methyl, (1,3-dimethylbutoxyamino)methyl, (2,2-dimethylbutoxyamino)methyl, (2,3-dimethylbutoxyamino)methyl, (3,3-dimethylbutoxyamino)methyl, (1-ethylbutoxyamino)methyl, (2-ethylbutoxyamino)methyl, (1,1,2-trimethylpropoxyamino)methyl, (1,2,2-trimethylpropoxyamino)methyl, (1-ethyl-1-methylpropoxyamino)methyl, (1-ethyl-2-methylpropoxyamino)methyl, methoxyaminoethyl, ethoxyaminoethyl, n-propoxyaminoethyl, (1-methylethoxyamino)ethyl, n-butoxyaminoethyl, (1-methylpropoxyamino)ethyl, (2-methylpropoxyamino)ethyl, (1,1-dimethylethoxyamino)ethyl, n-pentoxyaminoethyl, (1-methylbutoxyamino)ethyl, (2-methylbutoxyamino)ethyl, (3-methylbutoxyamino)ethyl, (2,2-dimethylpropoxyamino)ethyl, (1-ethylpropoxyamino)ethyl, n-hexoxyaminoethyl, (1,1-dimethylpropoxyamino)ethyl, (1,2-dimethylpropoxyamino)ethyl, (1-methylpentoxyamino)ethyl, (2-methylpentoxyamino)ethyl, (3-methylpentoxyamino)ethyl, (4-methylpentoxyamino)ethyl, (1,1-dimethylbutoxyamino)ethyl, (1,2-dimethylbutoxyamino)ethyl, (1,3-dimethylbutoxyamino)ethyl, (2,2-dimethylbutoxyamino)ethyl, (2,3-dimethylbutoxyamino)ethyl, (3,3-dimethylbutoxyamino)ethyl, (1-ethylbutoxyamino)ethyl, (2-ethylbutoxyamino)ethyl, (1,1,2-trimethylpropoxyamino)ethyl, (1,2,2-trimethylpropoxyamino)ethyl, (1-ethyl-1-methylpropoxyamino)ethyl, (1-ethyl-2-methylpropoxyamino)ethyl 2-(methoxyamino)propyl, 3-(methoxyamino)propyl or 2-(ethoxyamino)propyl, preferably C₁-C₆-alkoxyamino-C₁-C₂-alkyl;

C₁-C₆-alkoxy-C₁-C₆-alkylamino-C₁-C₆-alkyl: C₁-C₆-alkylamino-C₁-C₆-alkyl such as CH₂—NH—CH₃, CH₂—NH—C₂H₅, CH₂—NH—CH₂—C₂H₅, CH2—NH—CH(CH₃)₂, CH₂—NH—(CH₂)₃—CH₃, CH₂—NH—CH(CH₃)—C₂H₅, CH₂—NH—CH₂—CH (CH₃)₂, CH₂—NH—C(CH₃)₃, CH₂—NH—(CH₂)₄—CH₃, (1-methylbutylamino)methyl, (2-methylbutylamino)methyl, (3-methylbutylamino)methyl, (2,2-dimethylpropylamino)methyl, (1-ethylpropylamino)methyl, n-hexylamino-methyl, (1,1-dimethylpropylamino)methyl, (1,2-dimethylpropylamino)methyl, (1-methylpentylamino)methyl, (2-methylpentylamino)methyl, (3-methylpentylamino)methyl, (4-methylpentylamino)methyl, (1,1-dimethylbutylamino)methyl, (1,2-dimethylbutylamino)methyl, (1,3-dimethylbutylamino)methyl, (2,2-dimethylbutylamino)methyl, (2,3-dimethylbutylamino)methyl, (3,3-dimethylbutylamino)methyl, (1-ethylbutylamino)methyl, (2-ethylbutylamino)methyl, (1,1,2-trimethylpropylamino)methyl, (1,2,2-trimethylpropylamino)methyl, (1-ethyl-1-methylpropylamino)methyl, (1-ethyl-2-methylpropylamino)methyl, methylaminoethyl, ethylaminoethyl, n-propylaminoethyl, (1-methylethylamino)ethyl, n-butylaminoethyl, (1-methylpropylamino)ethyl, (2-methylpropylamino)ethyl, (1,1-dimethylethylamino)ethyl, n-pentylaminoethyl, (1-methylbutylamino)ethyl, (2-methylbutylamino)ethyl, (3-methylbutylamino)ethyl, (2,2-dimethylpropylamino)ethyl, (1-ethylpropylamino)ethyl, n-hexylaminoethyl, (1,1-dimethylpropylamino)ethyl, (1,2-dimethylpropylamino)ethyl, (1-methylpentylamino)ethyl, (2-methylpentylamino)ethyl, (3-methylpentylamino)ethyl, (4-methylpentylamino)ethyl, (1,1-dimethylbutylamino)ethyl, (1,2-dimethylbutylamino)ethyl, (1,3-dimethylbutylamino)ethyl, (2,2-dimethylbutylamino)ethyl, (2,3-dimethylbutylamino)ethyl, (3,3-dimethylbutylamino)ethyl, (1-ethylbutylamino)ethyl, (2-ethylbutylamino)ethyl, (1,1,2-trimethylpropylamino)ethyl, (1,2,2-trimethylpropylamino)ethyl, (1-ethyl-1-methylpropylamino)ethyl, (1-ethyl-2-methylpropylamino)ethyl, 2-(methylamino)propyl, 3-(methylamino)propyl and 2-(ethylamino)propyl, preferably C₁-C₆-alkylamino-C₁-C₂-alkyl, which is substituted by C₁-C₆-alkoxy as mentioned above, i.e., for example, CH₂—NH—CH₂—OCH₃ or CH₂—NH—CH₂—OC₂H₅;

C₁-C₆-alkyloximino-C₁-C₆-alkyl: C₁-C₆-alkyl which is substituted by C₁-C₆-alkyloximino such as methoxyimino, ethoxyimino, 1-propoxyimino, 2-propoxyimino, 1-methylethoxyimino, n-butoxyimino, sec-butoxyimino, tert-butoxyimino, 1-methyl-1-propoxyimino, 2-methyl-1-propoxyimino, 1-methyl-2-propoxyimino, 2-methyl-2-propoxyimino, n-pentoxyimino, 2-pentoxyimino, 3-pentoxyimino, 4-pentoxyimino, 1-methyl-1-butoxyimino, 2-methyl-1-butoxyimino, 3-methyl-1-butoxyimino, 1-methyl-2-butoxyimino, 2-methyl-2-butoxyimino, 3-methyl-2-butoxyimino, 1-methyl-3-butoxyimino, 2-methyl-3-butoxyimino, 3-methyl-3-butoxyimino, 1,1-dimethyl-2-propoxyimino, 1,2-dimethyl-1-propoxyimino, 1,2-dimethyl-2-propoxyimino, 1-ethyl-1-propoxyimino, 1-ethyl-2-propoxyimino, n-hexoxyimino, 2-hexoxyimino, 3-hexoxyimino, 4-hexoxyimino, 5-hexoxyimino, 1-methyl-1-pentoxyimino, 2-methyl-1-pentoxyimino, 3-methyl-1-pentoxyimino, 4-methyl-1-pentoxyimino, 1-methyl-2-pentoxyimino, 2-methyl-2-pentoxyimino, 3-methyl-2-pentoxyimino, 4-methyl-2-pentoxyimino, 1-methyl-3-pentoxyimino, 2-methyl-3-pentoxyimino, 3-methyl-3-pentoxyimino, 4-methyl-3-pentoxyimino, 1-methyl-4-pentoxyimino, 2-methyl-4-pentoxyimino, 3-methyl-4-pentoxyimino, 4-methyl-4-pentoxyimino, 1,1-dimethyl-2-butoxyimino, 1,1-dimethyl-3-butoxyimino, 1,2-dimethyl-1-butoxyimino, 1,2-dimethyl-2-butoxyimino, 1,2-dimethyl-3-butoxyimino, 1,3-dimethyl-1-butoxyimino, 1,3-dimethyl-2-butoxyimino, 1,3-dimethyl-3-butoxyimino, 2,2-dimethyl-3-butoxyimino, 2,3-dimethyl-1-butoxyimino, 2,3-dimethyl-2-butoxyimino, 2,3-dimethyl-3-butoxyimino, 3,3-dimethyl-1-butoxyimino, 3, 3-dimethyl-2-butoxyimino, 1-ethyl-1-butoxyimino, 1-ethyl-2-butoxyimino, 1-ethyl-3-butoxyimino, 2-ethyl-1-butoxyimino, 2-ethyl-2-butoxyimino, 2-ethyl-3-butoxyimino, 1,1,2-trimethyl-2-propoxyimino, 1-ethyl-1-methyl-2-propoxyimino, 1-ethyl-2-methyl-1-propoxyimino and 1-ethyl-2-methyl-2-propoxyimino, i.e., for example, methoxyiminomethyl;

C₁-C₆-alkoxy-C₁-C₆-alkyl: C₁-C₆-alkyl which is substituted by C₁-C₆-alkoxy as mentioned above, i.e., for example, CH₂—OCH₃, CH₂—OC₂H₅, n-propoxymethyl, CH₂—OCH(CH₃)₂, n-butoxymethyl, (1-methylpropoxy)methyl, (2-methylpropoxy)methyl, CH₂—OC(CH₃)₃, 2-(methoxy)ethyl, 2-(ethoxy)ethyl, 2-(n-propoxy)ethyl, 2-(1-methylethoxy)ethyl, 2-(n-butoxy)ethyl, 2-(1-methylpropoxy)ethyl, 2-(2-methylpropoxy)ethyl, 2-(1,1-dimethylethoxy)ethyl, 2-(methoxy)propyl, 2-(ethoxy)propyl, 2-(n-propoxy)propyl, 2-(1-methylethoxy)propyl, 2-(n-butoxy)propyl, 2-(1-methylpropoxy)propyl, 2-(2-methylpropoxy)propyl, 2-(1,1-dimethylethoxy)propyl, 3-(methoxy)propyl, 3-(ethoxy)propyl, 3-(n-propoxy)propyl, 3-(1-methylethoxy)propyl, 3-(n-butoxy)propyl, 3-(1-methylpropoxy)propyl, 3-(2-methylpropoxy)propyl, 3-(1,1-dimethylethoxy)propyl, 2-(methoxy)butyl, 2-(ethoxy)butyl, 2-(n-propoxy)butyl, 2-(1-methylethoxy)butyl, 2-(n-butoxy)butyl, 2-(1-methylpropoxy)butyl, 2-(2-methylpropoxy)butyl, 2-(1,1-dimethylethoxy)butyl, 3-(methoxy)butyl, 3-(ethoxy)butyl, 3-(n-propoxy)butyl, 3-(1-methylethoxy)butyl, 3-(n-butoxy)butyl, 3-(1-methylpropoxy)butyl, 3-(2-methylpropoxy)butyl, 3-(1,1-dimethylethoxy)butyl, 4-(methoxy)butyl, 4-(ethoxy)butyl, 4-(n-propoxy)butyl, 4-(1-methylethoxy)butyl, 4-(n-butoxy)butyl, 4-(1-methylpropoxy)butyl, 4-(2-methylpropoxy)butyl or 4-(1,1-dimethylethoxy)butyl, in particular CH₂—OCH₃ or 2-methoxyethyl;

di(C₁-C₆-alkoxy)—C₁-C₆-alkyl: for example 2,2-dimethoxyethyl or 2,2-diethoxyethyl;

C₁-C₆-alkoxy-C₁-C₆-alkoxy: C₁-C₆-alkoxy which is substituted by C₁-C₆-alkoxy as mentioned above, i.e., for example, OCH₂—OCH₃, OCH₂—OC₂H₅, n-propoxymethoxy, OCH₂—OCH(CH₃)₂, n-butoxymethoxy, (1-methylpropoxy)methoxy, (2-methylpropoxy)methoxy, OCH₂—OC(CH₃)₃, 2-(methoxy)ethoxy, 2-(ethoxy)ethoxy, 2-(n-propoxy)ethoxy, 2-(1-methylethoxy)ethoxy, 2-(n-butoxy)ethoxy, 2-(1-methylpropoxy)ethoxy, 2-(2-methylpropoxy)ethoxy, 2-(1,1-dimethylethoxy)ethoxy, 2-(methoxy)propoxy, 2-(ethoxy)propoxy, 2-(n-propoxy)propoxy,. 2-(1-methylethoxy)propoxy, 2-(n-butoxy)propoxy, 2-(1-methylpropoxy)propoxy, 2-(2-methylpropoxy)propoxy, 2-(1,1-dimethylethoxy)propoxy, 3-(methoxy)propoxy, 3-(ethoxy)propoxy, 3-(n-propoxy)propoxy, 3-(1-methylethoxy)propoxy, 3-(n-butoxy)propoxy, 3-(1-methylpropoxy)propoxy, 3-(2-methylpropoxy)propoxy, 3-(1,1-dimethylethoxy)propoxy, 2-(methoxy)butoxy, 2-(ethoxy)butoxy, 2-(n-propoxy)butoxy, 2-(1-methylethoxy)butoxy, 2-(n-butoxy)butoxy, 2-(1-methylpropoxy)butoxy, 2-(2-methylpropoxy)butoxy, 2-(1,1-dimethylethoxy)butoxy, 3-(methoxy)butoxy, 3-(ethoxy)butoxy, 3-(n-propoxy)butoxy, 3-(1-methylethoxy)butoxy, 3-(n-butoxy)butoxy, 3-(1-methylpropoxy)butoxy, 3-(2-methylpropoxy)butoxy, 3-(1,1-dimethylethoxy)butoxy, 4-(methoxy)butoxy, 4-(ethoxy)butoxy, 4-(n-propoxy)butoxy, 4-(1-methylethoxy)butoxy, 4-(n-butoxy)butoxy, 4-(1-methylpropoxy)butoxy, 4-(2-methylpropoxy)butoxy, 4-(1,1-dimethylethoxy)butoxy, 5-(methoxy)pentoxy, 5-(ethoxy)pentoxy, 5-(n-propoxy)pentoxy, 5-(1-methylethoxy)pentoxy, 5-(n-butoxy)pentoxy, 5-(1-methylpropoxy)pentoxy, 5-(2-methylpropoxy)pentoxy, 5-(1,1-dimethylethoxy)pentoxy, 6-(methoxy)hexoxy, 6-(ethoxy)hexoxy, 6-(n-propoxy)hexoxy, 6-(1-methylethoxy)hexoxy, 6-(n-butoxy)hexoxy, 6-(1-methylpropoxy)hexoxy, 6-(2-methylpropoxy)hexoxy or 6-(1,1-dimethylethoxy)hexoxy, in particular OCH₂—OCH₃ or OCH₂—OC₂H₅;

(C₁-C₆-alkyl)carbonyl-C₁-C₆-alkoxy: C₁-C₆-alkoxy which is substituted by (C₁-C₆-alkyl)carbonyl as mentioned above, i.e., for example, OCH₂—CO—CH₃, OCH₂—CO—C₂H₅, OCH₂—CO—CH₂—C₂H₅, OCH₂—CO—CH(CH₃)₂, n-butylcarbonyl-methoxy, 1-(CO—CH₃)ethoxy, 2-(CO—CH₃)ethoxy, 2-(CO—C₂H₅)ethoxy, 2-(CO—CH₂—C₂H₅)ethoxy, 2-(n-butylcarbonyl)ethoxy, 3-(CO—CH₃)propoxy, 3-(CO—C₂H₅)-propoxy, 3-(CO—CH₂—C₂H₅)propoxy, 3-(n-butylcarbonyl)propoxy, 4-(CO—CH₃)butoxy, 4-(CO—C₂H₅)butoxy, 4-(CO—CH₂—C₂H₅)butoxy, 4-(n-butylcarbonyl)butoxy, 5-(CO—CH₃)pentoxy, 5-(CO—C₂H₅)pentoxy, 5-(CO—CH₂—C₂H₅)pentoxy, 5-(n-butylcarbonyl)butoxy, 6-(CO—CH₃)hexoxy, 6-(CO—C₂H₅)hexoxy, 6-(CO—CH₂—C₂H₅)hexoxy or 6-(n-butylcarbonyl)hexoxy, in particular OCH₂—CO—OCH₃ or 1-(CO—CH₃)ethoxy;

(C₁-C₆-alkoxy)carbonyl-C₁-C₆-alkoxy: C₁-C₆-alkoxy which is substituted by (C₁-C₆-alkoxy)carbonyl as mentioned above, i.e., for example, OCH₂—CO—OCH₃, OCH₂—CO—OC₂H₅, OCH₂—CO—OCH₂—C₂H₅, OCH₂—CO—OCH(CH₃)₂, n-butoxycarbonylmethoxy, 1-(methoxycarbonyl)ethoxy, 2-(methoxycarbonyl)ethoxy, 2-(ethoxycarbonyl)ethoxy, 2-(n-propoxycarbonyl)ethoxy, 2-(n-butoxycarbonyl)ethoxy, 3-(methoxycarbonyl)propoxy, 3-(ethoxycarbonyl)propoxy, 3-(n-propoxycarbonyl)propoxy, 3-(n-butoxycarbonyl)propoxy, 4-(methoxycarbonyl)butoxy, 4-(ethoxycarbonyl)butoxy, 4-(n-propoxycarbonyl)butoxy, 4-(n-butoxycarbonyl)butoxy, 5-(methoxycarbonyl)pentoxy, 5-(ethoxycarbonyl)pentoxy, 5-(n-propoxycarbonyl)pentoxy, 5-(n-butoxycarbonyl)butoxy, 6-(methoxycarbonyl)hexoxy, 6-(ethoxycarbonyl)hexoxy, 6-(n-propoxycarbonyl)hexoxy or 6-(n-butoxycarbonyl)hexoxy, in particular OCH₂—CO—OCH₃ or 1-(methoxycarbonyl)ethoxy;

(C₁-C₆-alkoxy)carbonyl-C₁-C₆-alkyl: C₁-C₆-alkyl which is substituted by (C₁-C₆-alkoxy)carbonyl as mentioned above, i.e., for example, methoxycarbonylmethyl, ethoxycarbonylmethyl, 1-(methoxycarbonyl)ethyl, 2-(methoxycarbonyl)ethyl, 2-(ethoxycarbonyl)ethyl, 3-(methoxycarbonyl)propyl, 4-(methoxycarbonyl)butyl, 5-(methoxycarbonyl)pentyl or 6-(methoxycarbonyl)hexyl;

(C₁-C₆-alkoxy)carbonyl-C₁-C₆-alkylsulfonyl: C₁-C₆-alkylsulfonyl which is substituted by (C₁-C₆-alkoxy)carbonyl as mentioned above, i.e., for example, methoxycarbonylmethylsulfonyl, ethoxycarbonylmethylsulfonyl, 1-(methoxycarbonyl)ethylsulfonyl, 2-(methoxycarbonyl)ethylsulfonyl, 2-(ethoxycarbonyl)ethylsulfonyl, 3-(methoxycarbonyl)propylsulfonyl, 4-(methoxycarbonyl)butylsulfonyl, 5-(methoxycarbonyl)pentylsulfonyl or 6-(methoxycarbonyl)hexylsulfonyl;

C₁-C₆-alkylthio-C₁-C₆-alkyl: C₁-C₆-alkyl which is substituted by C₁-C₆-alkylthio as mentioned above, i.e., for example, CH₂—SCH₃, CH₂—SC₂H₅, CH₂—SCH₂—C₂H₅, CH₂—SCH(CH₃)₂, n-butylthiomethyl, CH₂—SCH(CH₃)—C₂H₅, CH₂—SCH₂—CH(CH₃)₂, CH₂—SC(CH₃)₃, 2-(SCH₃)ethyl, 2-(SC₂H₅)ethyl, 2-(SCH₂—C₂H₅)ethyl, 2-[SCH(CH₃)₂]ethyl, 2-(n-butylthio)ethyl, 2-[SCH(CH₃)—C₂H₅]ethyl, 2-(2-methylpropylthio)ethyl, 2-[SC(CH₃)₃]ethyl, 2-(SCH₃)propyl, 3-(SCH₃)propyl, 2-(SC₂H₅)propyl, 3-(SC₂H₅)propyl, 3-(SCH₂—C₂H₅)propyl, 3-(butylthio)propyl, 4-(SCH₃)butyl, 4-(SC₂H₅)butyl, 4-(SCH₂—C₂H₅)butyl or 4-(n-butylthio)butyl, in particular 2-(SCH₃)ethyl;

C₁-C₆-alkylthio-C₁-C₆-alkoxy: C₁-C₆-alkoxy-which is substituted by C₁-C₆-alkylthio as mentioned above, i.e., for example, OCH₂—SCH₃, OCH₂—SC₂H₅, OCH₂—SCH₂—C₂H₅, OCH₂—SCH(CH₃)₂, n-butylthiomethoxy, OCH₂—SCH(CH₃)—C₂H₅, OCH₂—SCH₂—CH(CH₃)₂, OCH₂—SC(CH₃)₃, 2-(SCH₃)ethoxy, 2-(SC₂H₅)ethoxy, 2-(SCH₂—C₂H₅)ethoxy, 2-[SCH(CH₃)₂]ethoxy, 2-(n-butylthio)ethoxy, 2-[SCH(CH₃)—C₂H₅]ethoxy, 2-(2-methylpropylthio)ethoxy, 2-[SC(CH₃)₃]ethoxy, 2-(SCH₃)propoxy, 3-(SCH₃)propoxy, 2-(SC₂H₅)propoxy, 3-(SC₂H₅)propoxy, 3-(SCH₂—C₂H₅)propoxy, 3-(butylthio)propoxy, 4-(SCH₃)butoxy, 4-(SC₂H₅)butoxy, 4-(CH₂—C₂H₅)butoxy or 4-(n-butylthio)butoxy, in particular 2-(SCH₃)ethoxy;

C₁-C₆-alkylthio-(C₁-C₆-alkyl)carbonyl: (C₁-C₆-alkyl)carbonyl which is substituted by C₁-C₆-alkylthio as mentioned above, preferably by SCH₃ or SC₂H₅, i.e., for example, methylthiomethylcarbonyl, ethylthiomethylcarbonyl, 1-(methylthio)ethylcarbonyl, 2-(methylthio)ethylcarbonyl, 3-(methylthio)propylcarbonyl, 4-(methylthio)butylcarbonyl, 5-(methylthio)pentylcarbonyl or 6-(methylthio)hexylcarbonyl, in particular CO—CH₂—SCH₃ or CO—CH(CH₃)—SCH₃; di(C₁-C₆-alkyl)amino-C₁-C₆-alkoxy: C₁-C₆-alkoxy which is substituted by di(C₁-C₆-alkyl)amino such as N(CH₃)₂, N(C₂H₅)₂, N,N-dipropylamino, N,N-di(1-methylethyl)amino, N,N-dibutylamino, N,N-di(1-methylpropyl)amino, N,N-di(2-methylpropyl)amino, N[C(CH₃)₃]₂, N-ethyl-N-methylamino, N-methyl-N-propylamino, N-methyl-N-(1-methylethyl)amino, N-butyl-N-methylamino, N-methyl-N-(1-methylpropyl)amino, N-methyl-N-(2-methylpropyl)amino, N-(1,1-dimethylethyl)-N-methylamino, N-ethyl-N-propylamino, N-ethyl-N-(1-methylethyl)amino, N-butyl-N-ethylamino, N-ethyl-N-(1-methylpropyl)amino, N-ethyl-N-(2-methylpropyl)amino, N-ethyl-N-(1,1-dimethylethyl)amino, N-(1-methylethyl)-N-propylamino, N-butyl-N-propylamino, N-(1-methylpropyl)-N-propylamino, N-(2-methylpropyl)-N-propylamino, N-(1,1-dimethylethyl)-N-propylamino, N-butyl-N-(1-methylethyl)amino, N-(1-methylethyl)-N-(1-methylpropyl)amino, N-(1-methylethyl)-N-(2-methylpropyl)amino, N-(1,1-dimethylethyl)-N-(1-methylethyl)amino, N-butyl-N-(1-methylpropyl)amino, N-butyl-N-(2-methylpropyl)amino, N-butyl-N-(1,1-dimethylethyl)amino, N-(1-methylpropyl)-N-(2-methylpropyl)amino, N-(1,1-dimethylethyl)-N-(1-methylpropyl)amino or N-(1,1-dimethylethyl)-N-(2-methylpropyl)amino, preferably by N,N-dimethylamino or N,N-diethylamino, i.e., for example, OCH₂—N(CH₃)₂, OCH₂—N(C₂H₅)₂, OCH(CH₃)—N(CH₃)₂, 2-(dimethylamino)ethoxy, OCH(CH₃)—N(C₂H₅)₂, 3-(dimethylamino)propoxy, 4-(dimethylamino)butoxy, 5-(dimethylamino)pentoxy or 6-(dimethylamino)hexoxy, in particular OCH₂—N(CH₃)₂ or OCH(CH₃)—N(CH₃)₂;

C₃-C₆-alkenyl: for example prop-2-en-1-yl, n-buten-4-yl, 1-methylprop-2-en-1-yl, 2-methylprop-2-en-1-yl, 2-buten-1-yl, n-penten-3-yl, n-penten-4-yl, 1-methylbut-2-en-1-yl, 2-methylbut-2-en-1-yl, 3-methylbut-2-en-1-yl, 1-methylbut-3-en-1-yl, 2-methylbut-3-en-1-yl, 3-methylbut-3-en-1-yl, 1,1-dimethylprop-2-en-1-yl, 1,2-dimethylprop-2-en-1-yl, 1-ethylprop-2-en-1-yl, n-hex-3-en-1-yl, n-hex-4-en-1-yl, n-hex-5-en-1-yl, 1-methylpent-3-en-1-yl, 2-methylpent-3-en-1-yl, 3-methylpent-3-en-1-yl, 4-methylpent-3-en-1-yl, 1-methylpent-4-en-1-yl, 2-methylpent-4-en-1-yl, 3-methylpent-4-en-1-yl, 4-methylpent-4-en-1-yl, 1,1-dimethylbut-2-en-1-yl, 1,1-dimethylbut-3-en-1-yl, 1,2-dimethylbut-2-en-1-yl, 1,2-dimethylbut-3-en-1-yl, 1,3-dimethylbut-2-en-1-yl, 1,3-dimethylbut-3-en-1-yl, 2,2-dimethylbut-3-en-1-yl, 2,3-dimethylbut-2-en-1-yl, 2,3-dimethylbut-3-en-1-yl, 3,3-dimethylbut-2-en-1-yl, 1-ethylbut-2-en-1-yl, 1-ethylbut-3-en-1-yl, 2-ethylbut-2-en-1-yl, 2-ethylbut-3-en-1-yl, 1,1,2-trimethylprop-2-en-1-yl, 1-ethyl-1-methylprop-2-en-1-yl or 1-ethyl-2-methylprop-2-en-1-yl, in particular prop-2-en-1-yl or n-buten-4-yl;

C₂-C₆-alkenyl: ethenyl or one of the radicals mentioned under C₃-C₆-alkenyl, in particular ethenyl or prop-2-en-1-yl;

C₃-C₆-alkenyloxy: prop-1-en-1-yloxy, prop-2-en-1-yloxy, 1-methylethenyloxy, n-buten-1-yloxy, n-buten-2-yloxy, n-buten-3-yloxy, 1-methylprop-1-en-1-yloxy, 2-methylprop-1-en-1-yloxy, 1-methylprop-2-en-1-yloxy, 2-methylprop-2-en-1-yloxy, n-penten-1-yloxy, n-penten-2-yloxy, n-penten-3-yloxy, n-penten-4-yloxy, 1-methylbut-1-en-1-yloxy, 2-methylbut-1-en-1-yloxy, 3-methylbut-1-en-1-yloxy, 1-methylbut-2-en-1-yloxy, 2-methylbut-2-en-1-yloxy, 3-methylbut-2-en-1-yloxy, 1-methylbut-3-en-1-yloxy, 2-methylbut-3-en-1-yloxy, 3-methylbut-3-en-1-yloxy, 1,1-dimethylprop-2-en-1-yloxy, 1,2-dimethylprop-1-en-1-yloxy, 1,2-dimethylprop-2-en-1-yloxy, 1-ethylprop-1-en-2-yloxy, 1-ethylprop-2-en-1-yloxy, n-hex-1-en-1-yloxy, n-hex-2-en-1-yloxy, n-hex-3-en-1-yloxy, n-hex-4-en-1-yloxy, n-hex-5-en-1-yloxy, 1-methylpent-1-en-1-yloxy, 2-methylpent-1-en-1-yloxy, 3-methylpent-1-en-1-yloxy, 4-methylpent-1-en-1-yloxy, 1-methylpent-2-en-1-yloxy, 2-methylpent-2-en-1-yloxy, 3-methylpent-2-en-1-yloxy, 4-methylpent-2-en-1-yloxy, 1-methylpent-3-en-1-yloxy, 2-methylpent-3-en-1-yloxy, 3-methylpent-3-en-1-yloxy, 4-methylpent-3-en-1-yloxy, 1-methylpent-4-en-1-yloxy, 2-methylpent-4-en-1-yloxy, 3-methylpent-4-en-1-yloxy, 4-methylpent-4-en-1-yloxy, 1,1-dimethylbut-2-en-1-yloxy, 1,1-dimethylbut-3-en-1-yloxy, 1,2-dimethylbut-1-en-1-yloxy, 1,2-dimethylbut-2-en-1-yloxy, 1,2-dimethylbut-3-en-1-yloxy, 1,3-dimethylbut-1-en-1-yloxy, 1,3-dimethylbut-2-en-1-yloxy, 1,3-dimethylbut-3-en-1-yloxy, 2,2-dimethylbut-3-en-1-yloxy, 2,3-dimethylbut-1-en-1-yloxy, 2,3-dimethylbut-2-en-1-yloxy, 2,3-dimethylbut-3-en-1-yloxy, 3,3-dimethylbut-1-en-1-yloxy, 3,3-dimethylbut-2-en-1-yloxy, 1-ethylbut-1-en-1-yloxy, 1-ethylbut-2-en-1-yloxy, 1-ethylbut-3-en-1-yloxy, 2-ethylbut-1-en-1-yloxy, 2-ethylbut-2-en-1-yloxy, 2-ethylbut-3-en-1-yloxy, 1,1,2-trimethylprop-2-en-1-yloxy, 1-ethyl-1-methylprop-2-en-1-yloxy, 1-ethyl-2-methylprop-1-en-1-yloxy or 1-ethyl-2-methylprop-2-en-1-yloxy, in particular prop-2-en-1-yloxy;

C₂-C₆-alkenyloxy: ethenyloxy or one of the radicals mentioned under C₃-C₆-alkenyloxy, in particular ethenyloxy or prop-2-ene-1-yloxy;

C₃-C₆-haloalkenyloxy: C₃-C₆-alkenyloxy as mentioned above which is partially or fully substituted by fluorine, chlorine and/or bromine, i.e., for example, 2-chloroallyloxy, 3-chloroallyloxy, 2,3-dichloroallyloxy, 3,3-dichloroallyloxy, 2,3,3-trichloroallyloxy, 2,3-dichlorobut-2-enyloxy, 2-bromoallyloxy, 3-bromoallyloxy, 2,3-dibromoallyloxy, 3,3-dibromoallyloxy, 2,3,3-tribromoallyloxy or 2,3-dibromobut-2-enyloxy, in particular 2-chloroallyloxy or 3,3-dichloroallyloxy;

C₂-C₆-alkenylthio: ethenylthio, prop-1-en-1-ylthio, prop-2-en-1-ylthio, 1-methylethenylthio, n-buten-1-ylthio, n-buten-2-ylthio, n-buten-3-ylthio, 1-methylprop-1-en-1-ylthio, 2-methylprop-1-en-1-ylthio, 1-methylprop-2-en-1-ylthio, 2-methylprbp-2-en-1-ylthio, n-penten-1-ylthio, n-penten-2-ylthio, n-penten-3-ylthio, n-penten-4-ylthio, 1-methylbut-1-en-1-ylthio, 2-methylbut-1-en-1-ylthio, 3-methylbut-1-en-1-ylthio, 1-methylbut-2-en-1-ylthio, 2-methylbut-2-en-1-ylthio, 3-methylbut-2-en-1-ylthio, 1-methylbut-3-en-1-ylthio, 2-methylbut-3-en-1-ylthio, 3-methylbut-3-en-1-ylthio, 1,1-dimethylprop-2-en-1-ylthio, 1,2-dimethylprop-1-en-1-ylthio, 1,2-dimethylprop-2-en-1-ylthio, 1-ethylprop-1-en-2-ylthio, 1-ethylprop-2-en-1-ylthio, n-hex-1-en-1-ylthio, n-hex-2-en-1-ylthio, n-hex-3-en-1-ylthio, n-hex-4-en-1-ylthio, n-hex-5-en-1-ylthio, 1-methylpent-1-en-1-ylthio, 2-methylpent-1-en-1-ylthio, 3-methylpent-1-en-1-ylthio, 4-methylpent-1-en-1-ylthio, 1-methylpent-2-en-1-ylthio, 2-methylpent-2-en-1-ylthio, 3-methylpent-2-en-1-ylthio, 4-methylpent-2-en-1-ylthio, 1-methylpent-3-en-1-ylthio, 2-methylpent-3-en-1-ylthio, 3-methylpent-3-en-1-ylthio, 4-methylpent-3-en-1-ylthio, 1-methylpent-4-en-1-ylthio, 2-methylpent-4-en-1-ylthio, 3-methylpent-4-en-1-ylthio, 4-methylpent-4-en-1-ylthio, 1,1-dimethylbut-2-en-1-ylthio, 1,1-dimethylbut-3-en-1-ylthio, 1,2-dimethylbut-1-en-1-ylthio, 1,2-dimethylbut-2-en-1-ylthio, 1,2-dimethylbut-3-en-1-ylthio, 1,3-dimethylbut-1-en-1-ylthio, 1,3-dimethylbut-2-en-1-ylthio, 1,3-dimethylbut-3-en-1-ylthio, 2,2-dimethylbut-3-en-1-ylthio, 2,3-dimethylbut-1-en-1-ylthio, 2,3-dimethylbut-2-en-1-ylthio, 2,3-dimethylbut-3-en-1-ylthio, 3,3-dimethylbut-1-en-1-ylthio, 3,3-dimethylbut-2-en-1-ylthio, 1-ethylbut-1-en-1-ylthio, 1-ethylbut-2-en-1-ylthio, 1-ethylbut-3-en-1-ylthio, 2-ethylbut-1-en-1-ylthio, 2-ethylbut-2-en-1-ylthio, 2-ethylbut-3-en-1-ylthio, 1,1,2-trimethylprop-2-en-1-ylthio, 1-ethyl-1-methylprop-2-en-1-ylthio, 1-ethyl-2-methylprop-1-en-1-ylthio or 1-ethyl-2-methylprop-2-en-1-ylthio, in particular ethenylthio or prop-2-en-1-ylthio;

C₃-C₆-alkynyl: prop-1-yn-1-yl, prop-2-yn-1-yl, n-but-1-yn-1-yl, n-but-1-yn-3-yl, n-but-1-yn-4-yl, n-but-2-yn-1-yl, n-pent-1-yn-1-yl, n-pent-1-yn-3-yl, n-pent-1-yn-4-yl, n-pent-1-yn-5-yl, n-pent-2-yn-1-yl, n-pent-2-yn-4-yl, n-pent-2-yn-5-yl, 3-methylbut-1-yn-3-yl, 3-methylbut-1-yn-4-yl, n-hex-1-yn-1-yl, n-hex-1-yn-3-yl, n-hex-1-yn-4-yl, n-hex-1-yn-5-yl, n-hex-1-yn-6-yl, n-hex-2-yn-1-yl, n-hex-2-yn-4-yl, n-hex-2-yn-5-yl, n-hex-2-yn-6-yl, n-hex-3-yn-1-yl, n-hex-3-yn-2-yl, 3-methylpent-1-yn-1-yl, 3-methylpent-1-yn-3-yl, 3-methylpent-1-yn-4-yl, 3-methylpent-1-yn-5-yl, 4-methylpent-1-yn-1-yl, 4-methylpent-2-yn-4-yl or 4-methylpent-2-yn-5-yl, in particular prop-2-yn-1-yl;

C₂-C₆-alkynyl: ethynyl or one of the radicals mentioned under C₃-C₆-alkynyl, in particular ethynyl or prop-2-yn-1-yl;

C₃-C₆-alkynyloxy: prop-1-yn-1-yloxy, prop-2-yn-1-yloxy, n-but-1-yn-1-yloxy, n-but-1-yn-3-yloxy, n-but-1-yn-4-yloxy, n-but-2-yn-1-yloxy, n-pent-1-yn-1-yloxy, n-pent-1-yn-3-yloxy, n-pent-1-yn-4-yloxy, n-pent-1-yn-5-yloxy, n-pent-2-yn-1-yloxy, n-pent-2-yn-4-yloxy, n-pent-2-yn-5-yloxy, 3-methylbut-1-yn-3-yloxy, 3-methylbut-1-yn-4-yloxy, n-hex-1-yn-1-yloxy, n-hex-1-yn-3-yloxy, n-hex-1-yn-4-yloxy, n-hex-1-yn-5-yloxy, n-hex-1-yn-6-yloxy, n-hex-2-yn-1-yloxy, n-hex-2-yn-4-yloxy, n-hex-2-yn-5-yloxy, n-hex-2-yn-6-yloxy, n-hex-3-yn-1-yloxy, n-hex-3-yn-2-yloxy, 3-methylpent-1-yn-1-yloxy, 3-methylpent-1-yn-3-yloxy, 3-methylpent-1-yn-4-yloxy, 3-methylpent-1-yn-5-yloxy, 4-methylpent-1-yn-1-yloxy, 4-methylpent-2-yn-4-yloxy or 4-methylpent-2-yn-5-yloxy, in particular prop-2-yn-1-yloxy;

C₂-C₆-alkynyloxy: ethynyloxy or one of the radicals mentioned under C₃-C₆-alkynyloxy, in particular ethynyloxy or prop-2-yn-1-yloxy;

C₃-C₆-alkynylthio: prop-1-yn-1-ylthio, prop-2-yn-1-ylthio, n-but-1-yn-1-ylthio, n-but-1-yn-3-ylthio, n-but-1-yn-4-ylthio, n-but-2-yn-1-ylthio, n-pent-1-yn-1-ylthio, n-pent-1-yn-3-ylthio, n-pent-1-yn-4-ylthio, n-pent-1-yn-5-ylthio, n-pent-2-yn-1-ylthio, n-pent-2-yn-4-ylthio, n-pent-2-yn-5-ylthio, 3-methylbut-1-yn-3-ylthio, 3-methylbut-1-yn-4-ylthio, n-hex-1-yn-1-ylthio, n-hex-1-yn-3-ylthio, n-hex-1-yn-4-ylthio, n-hex-1-yn-5-ylthio, n-hex-1-yn-6-ylthio, n-hex-2-yn-1-ylthio, n-hex-2-yn-4-ylthio, n-hex-2-yn-5-ylthio, n-hex-2-yn-6-ylthio, n-hex-3-yn-1-ylthio, n-hex-3-yn-2-ylthio, 3-methylpent-1-yn-1-ylthio, 3-methylpent-1-yn-3-ylthio, 3-methylpent-1-yn-4-ylthio, 3-methylpent-1-yn-5-ylthio, 4-methylpent-1-yn-1-ylthio, 4-methylpent-2-yn-4-ylthio or 4-methylpent-2-yn-5-ylthio, in particular prop-2-yn-1-ylthio;

C₂-C₆-alkynylthio: ethynylthio or one of the radicals mentioned under C₃-C₆-alkynylthio, in particular ethynylthio or prop-2-yn-1-ylthio;

(C₃-C₆-alkenyloxy)carbonyl: prop-1-en-1-yloxycarbonyl, prop-2-en-1-yloxycarbonyl, 1-methylethenyloxycarbonyl, n-buten-1-yloxycarbonyl, n-buten-2-yloxycarbonyl, n-buten-3-yloxycarbonyl, 1-methylprop-1-en-1-yloxycarbonyl, 2-methylprop-1-en-1-yloxycarbonyl, 1-methylprop-2-en-1-yloxycarbonyl, 2-methylprop-2-en-1-yloxycarbonyl, n-penten-1-yloxycarbonyl, n-penten-2-yloxycarbonyl, n-penten-3-yloxycarbonyl, n-penten-4-yloxycarbonyl, 1-methylbut-1-en-1-yloxycarbonyl, 2-methylbut-1-en-1-yloxycarbonyl, 3-methylbut-1-en-1-yloxycarbonyl, 1-methylbut-2-en-1-yloxycarbonyl, 2-methylbut-2-en-1-yloxycarbonyl, 3-methylbut-2-en-1-yloxycarbonyl, 1-methylbut-3-en-1-yloxycarbonyl, 2-methylbut-3-en-1-yloxycarbonyl, 3-methylbut-3-en-1-yloxycarbonyl, 1,1-dimethylprop-2-en-1-yloxycarbonyl, 1,2-dimethylprop-1-en-1-yloxycarbonyl, 1,2-dimethylprop-2-en-1-yloxycarbonyl, 1-ethylprop-1-en-2-yloxycarbonyl, 1-ethylprop-2-en-1-yloxycarbonyl, n-hex-1-en-1-yloxycarbonyl, n-hex-2-en-1-yloxycarbonyl, n-hex-3-en-1-yloxycarbonyl, n-hex-4-en-1-yloxycarbonyl, n-hex-5-en-1-yloxycarbonyl, 1-methylpent-1-en-1-yloxycarbonyl, 2-methylpent-1-en-1-yloxycarbonyl, 3-methylpent-1-en-1-yloxycarbonyl, 4-methylpent-1-en-1-yloxycarbonyl, 1-methylpent-2-en-1-yloxycarbonyl, 2-methylpent-2-en-1-yloxycarbonyl, 3-methylpent-2-en-1-yloxycarbonyl, 4-methylpent-2-en-1-yloxycarbonyl, 1-methylpent-3-en-1-yloxycarbonyl, 2-methylpent-3-en-1-yloxycarbonyl, 3-methylpent-3-en-1-yloxycarbonyl, 4-methylpent-3-en-1-yloxycarbonyl, 1-methylpent-4-en-1-yloxycarbonyl, 2-methylpent-4-en-1-yloxycarbonyl, 3-methylpent-4-en-1-yloxycarbonyl, 4-methylpent-4-en-1-yloxycarbonyl, 1,1-dimethylbut-2-en-1-yloxycarbonyl, 1,1-dimethylbut-3-en-1-yloxycarbonyl, 1,2-dimethylbut-1-en-1-yloxycarbonyl, 1,2-dimethylbut-2-en-1-yloxycarbonyl, 1,2-dimethylbut-3-en-1-yloxycarbonyl, 1,3-dimethylbut-1-en-1-yloxycarbonyl, 1,3-dimethylbut-2-en-1-yloxycarbonyl, 1,3-dimethylbut-3-en-1-yloxycarbonyl, 2,3-dimethylbut-3-en-1-yloxycarbonyl, 2,3-dimethylbut-1-en-1-yloxycarbonyl, 2,3-dimethylbut-2-en-1-yloxycarbonyl, 2,3-dimethylbut-3-en-1-yloxycarbonyl, 3, 3-dimethylbut-1-en-1-yloxycarbonyl, 3,3-dimethylbut-2-en-1-yloxycarbonyl, 1-ethylbut-2-en-1-yloxycarbonyl, 1-ethylbut-2-en-1-yloxycarbonyl, 1-ethylbut-3-en-1-yloxycarbonyl, 2-ethylbut-1-en-1-yloxycarbonyl, 2-ethylbut-2-en-1-yloxycarbonyl, 2-ethylbut-3-en-1-yloxycarbonyl, 1,1,2-trimethylprop-2-en-1-yloxycarbonyl, 1-ethyl-methylprop-2-en-1-yloxycarbonyl, 1-ethyl-2-methylprop-1-en-1-yloxycarbonyl or 1-ethyl-2-methylprop-2-en-1-yloxycarbonyl, in particular prop-2-en-1-yloxycarbonyl;

(C₃-C₆-alkenyloxy)carbonyl-C₁-C₆-alkyl: C₁-C₆-alkyl which is substituted by (C₃-C₆-alkenyloxy)carbonyl as mentioned above, preferably by prop-2-en-1-yl-oxycarbonyl, i.e., for example, prop-2-en-1-yl-oxycarbonyl-methyl; (C₂-C₆-alkenyl)carbonyloxy: ethenylcarbonyloxy, prop-1-en-1-ylcarbonyloxy, prop-2-en-1-ylcarbonyloxy, 1-methylethenylcarbonyloxy, n-buten-1-ylcarbonyloxy, n-buten-2-ylcarbonyloxy, n-buten-3-ylcarbonyloxy, 1-methylprop-1-en-1-ylcarbonyloxy, 2-methylprop-1-en-1-ylcarbonyloxy, 1-methylprop-2-en-1-ylcarbonyloxy, 2-methylprop-2-en-1-ylcarbonyloxy, n-penten-1-ylcarbonyloxy, n-penten-2-ylcarbonyloxy, n-penten-3-ylcarbonyloxy, n-penten-4-ylcarbonyloxy, 1-methylbut-1-en-1-ylcarbonyloxy, 2-methylbut-1-en-1-ylcarbonyloxy, 3-methylbut-1-en-1-ylcarbonyloxy, 1-methylbut-2-en-1-ylcarbonyloxy, 2-methylbut-2-en-1-ylcarbonyloxy, 3-methylbut-2-en-1-ylcarbonyloxy, 1-methylbut-3-en-1-ylcarbonyloxy, 2-methylbut-3-en-1-ylcarbonyloxy, 3-methylbut-3-en-1-ylcarbonyloxy, 1,1-dimethylprop-2-en-1-ylcarbonyloxy, 1,2-dimethylprop-1-en-1-ylcarbonyloxy, 1,2-dimethylprop-2-en-1-ylcarbonyloxy, 1-ethylprop-1-en-2-ylcarbonyloxy, 1-ethylprop-2-en-1-ylcarbonyloxy, n-hex-1-en-1-ylcarbonyloxy, n-hex-2-en-1-ylcarbonyloxy, n-hex-3-en-1-ylcarbonyloxy, n-hex-4-en-1-ylcarbonyloxy, n-hex-5-en-1-ylcarbonyloxy, 1-methylpent-1-en-1-ylcarbonyloxy, 2-methylpent-1-en-1-ylcarbonyloxy, 3-methylpent-1-en-1-ylcarbonyloxy, 4-methylpent-1-en-1-ylcarbonyloxy, 1-methylpent-2-en-1-ylcarbonyloxy, 2-methylpent-2-en-1-ylcarbonyloxy, 3-methylpent-2-en-1-ylcarbonyloxy, 4-methylpent-2-en-1-ylcarbonyloxy, 1-methylpent-3-en-1-ylcarbonyloxy, 2-methylpent-3-en-1-ylcarbonyloxy, 3-methylpent-3-en-1-ylcarbonyloxy, 4-methylpent-3-en-1-ylcarbonyloxy, 1-methylpent-4-en-1-ylcarbonyloxy, 2-methylpent-4-en-1-ylcarbonyloxy, 3-methylpent-4-en-1-ylcarbonyloxy, 4-methylpent-4-en-1-ylcarbonyloxy, 1,1-dimethylbut-2-en-1-ylcarbonyloxy, 1,1-dimethylbut-3-en-1-ylcarbonyloxy, 1,2-dimethylbut-1-en-1-ylcarbonyloxy, 1,2-dimethylbut-2-en-1-ylcarbonyloxy, 1,2-dimethylbut-3-en-1-ylcarbonyloxy, 1,3-dimethylbut-1-en-1-ylcarbonyloxy, 1,3-dimethylbut-2-en-1-ylcarbonyloxy, 1,3-dimethylbut-3-en-1-ylcarbonyloxy, 2,2-dimethylbut-3-en-1-ylcarbonyloxy, 2,3-dimethylbut-1-en-1-ylcarbonyloxy, 2,3-dimethylbut-2-en-1-ylcarbonyloxy, 2,3-dimethylbut-3-en-1-ylcarbonyloxy, 3,3-dimethylbut-1-en-1-ylcarbonyloxy, 3,3-dimethylbut-2-en-1-ylcarbonyloxy, 1-ethylbut-1-en-1-ylcarbonyloxy, 1-ethylbut-2-en-1-ylcarbonyloxy, 1-ethylbut-3-en-1-ylcarbonyloxy, 2-ethylbut-1-en-1-ylcarbonyloxy, 2-ethylbut-2-en-1-ylcarbonyloxy, 2-ethylbut-3-en-1-ylcarbonyloxy, 1,1,2-trimethylprop-2-en-1-ylcarbonyloxy, 1-ethyl-1-methylprop-2-en-1-ylcarbonyloxy, 1-ethyl-2-methylprop-1-en-1-ylcarbonyloxy or 1-ethyl-2-methylprop-2-en-1-ylcarbonyloxy, in particular ethenylcarbonyloxy or prop-2-en-1-ylcarbonyloxy;

(C₁-C₆-alkoxy)carbonyl-C₂-C₆-alkenyl: C₂-C₆-alkenyl which is substituted by (C₁-C₆-alkoxy)carbonyl as mentioned above, i.e., for example, methoxycarbonylprop-2-en-1-yl;

C₁-C₆-alkoxy-C₃-C₆-alkenyloxy: C₃-C₆-alkenyloxy which is substituted by C₁-C₆-alkoxy as mentioned above, i.e., for example, methylprop-2-en-1-yloxy;

C₃-C₆-alkenyloxy-C₁-C₆-alkyl: C₁-C₆-alkyl which is substituted by C₃-C₆-alkenyloxy as mentioned above, preferably by allyloxy, 2-methylprop-2-en-1-yloxy, but-1-en-3-yloxy, but-1-en-4-yloxy or but-2-en-1-yloxy, i.e., for example, allyloxymethyl, 2-allyloxyethyl or but-1-en-4-yloxymethyl;

C₃-C₆-alkynyloxy-C₁-C₆-alkyl: C₁-C₆-alkyl which is substituted by C₃-C₆-alkynyloxy as mentioned above, preferably by propargyloxy, but-1-yn-3-yloxy, but-1-yn-4-yloxy or but-2-yn-1-yloxy, i.e., for example, propargyloxymethyl or 2-propargyloxyethyl;

C₃-C₆-haloalkenyl: C₃-C₆-alkenyl as mentioned above, which is partially or fully substituted by fluorine, chlorine and/or bromine, i.e., for example, 2-chloroallyl, 3-chloroallyl, 2,3-dichloroallyl, 3,3-dichloroallyl, 2,3,3-trichloroallyl, 2,3-dichlorobut-2-enyl, 2-bromoallyl, 3-bromoallyl, 2,3-dibromoallyl, 3,3-dibromoallyl, 2,3,3-tribromoallyl or 2,3-dibromobut-2-enyl, in particular 2-chloroallyl or 3,3-dichloroallyl;

C₃-C₆-haloalkynyl: C₃-C₆-alkynyl as mentioned above which is partially or fully substituted by fluorine, chlorine and/or bromine, i.e., for example, 3-chloropropargyl, 3-bromopropargyl, 3-fluoropropargyl, 3,3,3-trifluoropropargyl, 4-chlorobut-2-ynyl, 4-bromobut-2-ynyl, 4,4,4-trifluorobut-2-ynyl, 1,4-dichlorobut-2-ynyl, 5-chloropent-3-ynyl, 5-fluoropent-3-ynyl, 5,5,5-trifluoropent-3-ynyl, 6-chlorohex-2-ynyl, preferably 3-chloropropargyl, 3,3,3-trifluoropropargyl, 4,4,4-trifluorobut-2-ynyl;

C₃-C₆-cycloalkyl-C₁-C₆-alkyl: cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, cycloheptylmethyl, cyclooctylmethyl, 1-(cyclopropyl)ethyl, 1-(cyclobutyl)ethyl, 1-(cyclopentyl)ethyl, 1-(cyclohexyl)ethyl, 2-(cyclopropyl)ethyl, 2-(cyclobutyl)ethyl, 2-(cyclopentyl)ethyl, 2-(cyclohexyl)ethyl, 2-(cyclopropyl)propyl, 3-(cyclopropyl)propyl, 3-(cyclobutyl)propyl, 3-(cyclopentyl)propyl, 3-(cyclohexyl)propyl, 2-(cyclopropyl)butyl, 3-(cyclopropyl)butyl, 4-(cyclopropyl)butyl, 4-(cyclobutyl)butyl, 4-(cyclopentyl)butyl, 4-(cyclohexyl)butyl, 2-(cyclopropyl)pentyl, 3-(cyclopropyl)pentyl, 4-(cyclopropyl)pentyl, 5-(cyclopropyl)pentyl, 2-(cyclobutyl)pentyl, 3-(cyclobutyl)pentyl, 5-(cyclobutyl)pentyl, 2-(cyclopropyl)hexyl, 3-(cyclopropyl)hexyl, 6-(cyclopropyl)hexyl, in particular cyclopentylmethyl or cyclohexylmethyl;

C₃-C₆-halocycloalkyl-C₁-C₆-alkyl: C₃-C₆-cycloalkyl-C₁-C₆-alkyl, as mentioned above which is partially or fully halogenated at the cycloalkylring, and preferably carries 1, 2, 3, 4 or 5 halogenatoms, especially fluorine or chlorine, i.e., for example perchlrocyclopropyl, perfluorocyclopropyl, 1-fluoro- or 1-chlorocyclopropyl, hexachlorocyclohexyl, etc.;

C₃-C₆-cycloalkoxy: cyclopropoxy, cyclobutoxy, cyclopentoxy, or cyclohexoxy;

C₃-C₆-cycloalkoxy-C₁-C₄-alkyl: cyclopropyloxymethyl, cyclobutyloxymethyl, cyclopentyloxymethyl, cyclohexyloxymethyl, 1-(cyclopropyloxy)ethyl, 1-(cyclobutyloxy)ethyl, 1-(cyclopentyloxy)ethyl, 1-(cyclohexyloxy)ethyl, 2-(cyclopropyloxy)ethyl, 2-(cyclobutyloxy)ethyl, 2-(cyclopentyloxy)ethyl, 2-(cyclohexyloxy)ethyl, 3-(cyclopropyloxy)propyl, 3-(cyclobutyloxy)propyl, 3-(cyclopentyloxy)propyl, 3-(cyclohexyloxy)propyl, 4-(cyclopropyloxy)butyl, 4-(cyclobutyloxy)butyl, 4-(cyclopentyloxy)butyl or 4-(cyclohexyloxy)butyl, in particular cyclopentyloxymethyl, cyclohexyloxymethyl or 2-(cyclopentyloxy)ethyl;

C₆-C₁₄-aromatic radicals: phenyl, naphthyl or anthracenyl or heteroaromatic radicals (aromatic heterocycyl) having-6 to 14 carbon ring atoms some of which, i.e. at least one, two, three, four or five, are replaced by heteroatoms selected from the group consisting of N, O and S. In addition, C₆-C₁₄-aromatic radicals can be attached via two adjacent carbon atoms to a 4- to 7-membered carbo- or heterocycle which can be saturated or partially unsaturated and which can, in addition to the carbon ring members, have one, two or three of the following hetero ring members: —O—, —S—, —S(O)₂—, —N═, —NH— or —N(C₁-C₆-alkyl)—. Furthermore, the C₆-C₁₄-aromatic radicals can be mono-, di-, tri-, tetra- or pentasubstituted by the atom groups defined above.

The N′-substituted N-amino urea derivatives of the formula II used as starting materials in the process according to the invention and processes for their preparation are known per se and described in the literature, for example in WO 94/10173, and reference is here made to the corresponding literature for more details.

With a view to their use for the preparation of compounds having herbicidal action, R is preferably a group of the formula:

CHO, CN, C(O)OR³, C(S)SR³, C(S)OR³, C(O)SR³, C(O)R², P(O)R¹OR¹, P(O)(OR¹)₂, S(O)₂R² or SO₂NHR^(1.)

In particular

C(O)OR³, C(S)SR³, C(S)OR³, C(O)SR³, and specifically C(O)OR³.

Independently of one another, the variables R¹to R⁷ are preferably as defined below:

R¹ is hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₃-alkoxy-C₁-C₃-alkyl, C₃-C₆-alkenyl or C₃-C₆-alkynyl;

R² is C₁-C₆-alkyl, C₃-C₆-cycloalkyl, C₃-C₆-alkenyl, C₃-C₆-alkynyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy-C₂-C₆-alkyl, C₁-C₆-alkoxycarbonyl-C₁-C₆-alkyl, C₁-C₆-alkylthio-C₁-C₆-alkyl, C₃-C₆-alkenyloxycarbonyl-C₁-C₆-alkyl, C₃-C₆-alkynyloxycarbonyl-C₁-C₆-alkyl, C₃-C₆-alkenyloxy-C₁-C₆-alkyl, C₃-C₆-alkynyloxy-C₁-C₆-alkyl, C₁-C₆-haloalkoxy-C₁-C₆-alkyl, cyano-C₁-C₆-alkyl, halo-C₂-C₆-alkenyl, halo-C₃-C₆-alkynyl, C₁-C₆-alkylcarbonyl, CHR¹COR⁷, P(O)(OR⁷)₂, CHR¹P(S)(OR⁷)₂, CHR¹C(O)NR⁴R⁵, CHR¹C(O)NH₂,

is benzyl, phenyl, phenoxy-C₁-C₆-alkyl or benzyloxy-C₁-C₆-alkyl, where the four last-mentioned substituents may be substituted by halogen, C₁-C₄-alkyl or C₁-C₄-haloalkyl;

R³ is C₁-C₁₅-alkyl, C₃-C₈-cycloalkyl, C₂-C₁₀-alkenyl, C₃-C₁₀-alkynyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy-C₁-C₆-alkyl, C₁-C₆-alkylthioalkyl, C₁-C₆-alkoxycarbonyl-C₁-C₆-alkyl, C₃-C₆-alkenyloxycarbonyl-C₁-C₆-alkyl, C₃-C₆-alkynyloxycarbonyl-C₁-C₆-alkyl, C₃-C₆-alkenyloxy-C₁-C₆-alkyl, C₁-C₆-haloalkoxy-C₁-C₆-alkyl, cyano-C₁-C₆-alkyl, halo-C₃-C₆-alkenyl, C₁-C₆-alkoxy-C₃-C₆-alkenyl, C₁-C₆-alkoxy-C₃-C₆-alkynyl, CHR¹COR⁷, P(O)(OR⁷)₂, CHR¹P(S)(OR⁷)₂, CHR¹C(O)NR⁴R⁵, CHR¹C(O)NH₂,

is benzyl, phenyl, phenoxy-C₁-C₆-alkyl or benzyloxy-C₁-C₆-alkyl, where the four last-mentioned substituents may be substituted by halogen, C₁-C₄-alkyl or C₁-C₄-haloalkyl;

R⁴ is hydrogen, C₁-C₆-alkyl or C₁-C₆-alkoxy;

R⁵, R⁶ independently of one another are hydrogen, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy-C₁-C₆-alkyl, C₁-C₆-alkoxycarbonyl-C₁-C₆-alkyl, C₁-C₆-alkoxycarbonyl-C₂-C₆-alkenyl,

are benzyl which may be mono- to pentasubstituted by halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio, C₁-C₄-alkoxycarbonyl, C₁-C₄-alkoxycarbonyl-C₁-C₄-alkyl, nitro or cyano, or

R⁴ and R⁵ together with the common nitrogen atom are a saturated or unsaturated 4- to 7-membered azaheterocycle which, in addition to the carbon ring members may, if desired, contain one of the following members: —O—, —S—, —N═, —NH— or —N(C₁-C₆-alkyl)—;

R⁷ is hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₃-alkoxy-C₁-C₃-alkyl, C₂-C₆-cyanoalkyl, C₃-C₆-alkenyl or C₃-C₆-alkynyl.

R¹ is, in particular: C₁-C₃-alkyl, C₁-C₃-haloalkyl, C₁-C₃-alkoxy-C₁-C₃-alkyl.

R² is, in particular: C₁-C₆-alkyl, C₃-C₆-cycloalkyl, C₃-C₄-alkenyl, C₃-C₄-alkynyl, C₁-C₃-haloalkyl, C₁-C₃-alkoxy-C₁-C₃-alkyl, C₁-C₃-alkoxycarbonyl-C₁-C₃-alkyl, cyano-C₁-C₃-alkyl, halo-C₂-C₄-alkenyl, halo-C₃-C₄-alkynyl, C₁-C₃-alkylcarbonyl, CHR¹COR⁷, P(O)(OR⁷)₂, CHR¹P(S)(OR⁷)₂, CHR¹C(O)NR⁴R⁵, CHR¹C(O)NH₂, C₁-C₃-alkyl, which is substituted by phenoxy or benzyloxy, benzyl or phenyl, which can be substituted by halogen, methyl or CF₃.

R³ is, in particular: C₁-C₁₅-alkyl, C₃-C₈-cycloalkyl, C₂-C₆-alkenyl, C₃-C₆-alkynyl, C₁-C₆-haloalkyl, C₁-C₃-alkoxy-C₁-C₃-alkyl, C₁-C₃-alkoxycarbonyl-C₁-C₃-alkyl, C₃-C₄-alkenyloxycarbonyl-C₁-C₃-alkyl, C₃-C₄-alkynyloxycarbonyl-C₁-C₃-alkyl, cyano-C₁-C₆-alkyl, halo-C₃-C₄-alkenyl, CHR¹COR⁷, P(O)(OR⁷)₂, CHR¹C(O)NR⁴R⁵, CHR¹C(O)NH₂, C₁-C₃-alkyl which is substituted by phenoxy or benzyloxy, benzyl or phenyl which can be substituted by halogen, methyl or CF₃.

The variable m has, in particular, the value 0; Z is preferably oxygen or sulfur, in particular oxygen.

Examples of preferred perhydrodiazines of the formula I are the compounds of the formula Ia in which R has the meanings given in Table 1.

TABLE 1 No. R 1 CO₂H 2 CHO 3 CN 4 C(O)NHCH₃ 5 C(O)NHC₂H₅ 6 C(O)NH-N-C₃H₇ 7 C(O)NH-i-C₃H₇ 8 C(O)NH-c-C₃H₅ 9 C(O)NHCH₂CH═CH₂ 10 C(O)NHCH₂—C≡CH 11 C(O)NHCH₂CH₂OCH₃ 12 C(O)NHCH₂CO₂CH₃ 13 C(O)NHCH(CH₃)CO₂CH₃ 14 C(O)N(CH₃)₂ 15 C(O)N(CH₃)C₂H₅ 16 C(O)NHCH₂C₆H₅ 17 C(O)N(CH₃)CH₂C₆H₅ 18 C(O)NH-2-Cl-benzyl 19 C(O)NH-3-Cl-benzyl 20 C(O)NH-4-Cl-benzyl 21 C(O)NH-2-CH₃-benzyl 22 C(O)NH-3-CH₃-benzyl 23 C(O)NH-4-CH₃-benzyl 24 C(O)NH-2,3-Cl₂-benzyl 25 C(O)NH-3,4-Cl₂-benzyl 26 C(O)NH-2,4-Cl₂-benzyl 27 C(O)NH-3-CF₃-benzyl 28 C(O)NH-4-CF₃-benzyl 29 C(O)NH-3-NO₂-benzyl 30 C(O)NH-4-NO₂-benzyl 31 C(O)N(CH₂)₅ 32 C(O)N(CH₂CH₂OCH₂CH₂) 33 C(O)N(CH₂CH₂N(CH₃)CH₂CH₂) 34 C(O)NHSO₂CH₃ 35 C(O)NHSO₂C₂H₅ 36 C(O)NHSO₂-n-C₃H₇ 37 C(O)NHSO₂-i-C₃H₇ 38 C(O)NHCO₂CH₃ 39 C(O)NHCO₂C₂H₅ 40 C(O)NHCO₂-n-C₃H₇ 41 C(O)NHCO₂-i-C₃H₇ 42 C(O)NHCO₂-c-C₃H₅ 43 C(O)NHSO₃CH₃ 44 C(O)NHSO₃C₂H₅ 45 C(O)NHSO₃-n-C₃H₇ 46 C(O)NHSO₃-i-C₃H₇ 47 C(O)NHSO₃-c-C₃H₅ 48 C(O)CH₃ 49 C(O)C₂H₅ 50 C(O)-n-C₃H₇ 51 C(O)-i-C₃H₇ 52 C(O)-c-C₃H₅ 53 C(O)-n-C₄H₉ 54 C(O)-sec-C₄H₉ 55 C(O)-i-C₄H₉ 56 C(O)-t-C₄H₉ 57 C(O)CH₂CH═CH₂ 58 C(O)CH₂C≡CH 59 C(O)-c-C₃H₅ 60 C(O)-c-C₅H₉ 61 C(O)CH₂Cl 62 C(O)CF₃ 63 C(O)CH₂CF₃ 64 C(O)CH₂OCH₃ 65 C(O)CH₂OC₂H₅ 66 C(O)CH₂CO₂CH₃ 67 C(O)CH₂CH₂CO₂CH₃ 68 C(O)CH₂CH₂CO₂CH₂CH═CH₂ 69 C(O)CH₂CH₂CO₂CH₂C≡CH 70 C(O)CH₂CN 71 C(O)CH₂CH₂CN 72 C(O)CH₂—C(Cl)═CH₂ 73 C(O)CH═CH₂ 74 C(O)CH₂C(O)CH₃ 75 C(O)CH₂P(O)(OCH₃)₂ 76 C(O)CH(CH₃)P(O)(OCH₃)₂ 77 C(O)CH₂C(O)N(CH₃)₂ 78 C(O)-benzyl 79 C(O)-3-CH₃-benzyl 80 C(O)-4-CH₃-benzyl 81 C(O)-3-Cl-benzyl 82 C(O)-4-Cl-benzyl 83 C(O)-3-CF₃-benzyl 84 C(O)-4-CF₃-benzyl 85 C(O)-phenyl 86 C(O)-3-CH₃-phenyl 87 C(O)-4-CH₃-phenyl 88 C(O)-3-Cl-phenyl 89 C(O)-4-Cl-phenyl 90 C(O)-3-CF₃-phenyl 91 C(O)-4-CF₃-phenyl 92 C(O)-2-pyridyl 93 C(O)-3-pyridyl 94 C(O)-4-pyridyl 95 P(O)(CH₃)OCH₃ 96 P(O)(C₂H₅)OCH₃ 97 P(O)(CH₃)OC₂H₅ 98 P(O)(CH₃)O-n-C₃H₇ 99 P(O)(OCH₃)₂ 100 P(O)(OC₂H₅)₂ 101 P(O)(OCH₃)OC₂H₅ 102 SOCH₃ 103 SOC₂H₅ 104 SO₂CH₃ 105 SO₂C₂H₅ 106 SO₂-n-C₃H₇ 107 SO₂-i-C₃H₇ 108 SO₂-c-C₃H₅ 109 SO₂-sec-C₄H₉ 110 SO₂—CH₂CH=CH₂ 111 SO₂CH₂Cl 112 SO₂CF₃ 113 SO₂CH₂CF₃ 114 SO₂CH₂OCH₃ 115 SO₂CH₂OC₂H₅ 116 SO₂CH₂CO₂CH₃ 117 SO₂CH₂CN 118 SO₂CH₂CH₂CN 119 SO₂CH=CH₂ 120 SO₂-benzyl 121 SO₂-3-CH₃-benzyl 122 SO₂-4-CH₃-benzyl 123 SO₂-3-Cl-benzyl 124 SO₂-4-Cl-benzyl 125 SO₂-3-CF₃-benzyl 126 SO₂-4-CF₃-benzyl 127 S(O)-phenyl 128 S(O)-3-Cl-phenyl 129 S(O)-4-Cl-phenyl 130 SO₂-3-Cl-phenyl 131 SO₂-4-Cl-phenyl 132 SO₂-3-CF₃-phenyl 133 SO₂-4-CF₃-phenyl 134 SO₂-3-CH₃-phenyl 135 SO₂-4-CH₃-phenyl 136 SO₂-3-pyridyl 137 SO₂-4-pyridyl 138 SO₂NH₂ 139 SO₂NHCH₃ 140 SO₂NHC₂H₅ 141 SO₂NH-i-C₃H₇ 142 SO₂NH-n-C₃H₇ 143 SO₂NHCH₂CH₂Cl 144 SO₂NH-t-C₄H₉ 145 SO₂NH-n-C₄H₉

In Table 1, i denotes “iso”, t denotes “tertiary” and c denotes “cyclo”.

Examples of preferred perhydrodiazines of the formula I are furthermore the compounds of the formula Ib in which R is as defined in Table 1.

(Compounds Ib No. 1-Ib No. 145)

Very particularly preferred compounds of the formula I are compounds of the formula Ib.1 in which R is COOR³, in particular those in which R³ has the meanings given in Table 2.

TABLE 2 No. R³ 1 CH₃ 2 C₂H₅ 3 n-C₃H₇ 4 i-C₃H₇ 5 c-C₃H₅ 6 n-C₄H₉ 7 i-C₄H₉ 8 sec-C₄H₉ 9 c-C₄H₇ 10 t-C₄H₉ 11 n-C₅H₁₁ 12 sec-C₅H₁₁ 13 2,2-dimethylpropyl 14 2-methylbutyl 15 3-methylbutyl 16 1,1-dimethylpropyl 17 1,2-dimethylpropyl 18 c-C₅H₉ 19 n-C₆H₁₃ 20 1,1-dimethylbutyl 21 1,2-dimethylbutyl 22 1,3-dimethylbutyl 23 2,2-dimethylbutyl 24 2,3-dimethylbutyl 25 3,3-dimethylbutyl 26 1-ethylpropyl 27 1-ethylbutyl 28 2-ethylbutyl 29 1,1,2-trimethylpropyl 30 1,2,2-trimethylpropyl 31 1-methylpentyl 32 1-ethyl-1-methylpropyl 33 1-ethyl-2-methylpropyl 34 c-C₆H₁₁ 35 n-C₇H₁₅ 36 1-methylhexyl 37 2-methylhexyl 38 3-methylhexyl 39 4-methylhexyl 40 5-methylhexyl 41 1-ethylpentyl 42 2-ethylpentyl 43 3-ethylpentyl 44 4-ethylpentyl 45 1,1-dimethylpentyl 46 1,2-dimethylpentyl 47 1,3-dimethylpentyl 48 1,4-dimethylpentyl 49 c-C₇H₁₃ 50 n-C₈H₁₇ 51 1-methylheptyl 52 2-methylheptyl 53 3-methylheptyl 54 4-methylheptyl 55 5-methylheptyl 56 6-methylheptyl 57 1-ethylhexyl 58 2-ethylhexyl 59 3-ethylhexyl 60 4-ethylhexyl 61 1,1-dimethylhexyl 62 1,2-dimethylhexyl 63 1,3-dimethylhexyl 64 1,4-dimethylhexyl 65 1,5-dimethylhexyl 66 c-C₈H15 67 n-C₉H₁₉ 68 1-methyloctyl 69 2-methyloctyl 70 3-methyloctyl 71 4-methyloctyl 72 5-methyloctyl 73 6-methyloctyl 74 7-methyloctyl 75 1-ethylheptyl 76 2-ethylheptyl 77 3-ethylheptyl 78 4-ethylheptyl 79 5-ethylheptyl 80 6-ethylheptyl 81 1,1-dimethylheptyl 82 1,2-dimethylheptyl 83 1,3-dimethylheptyl 84 1,4-dimethylheptyl 85 1,5-dimethylheptyl 86 1,6-dimethylheptyl 87 c-C₉H₁₇ 88 n-C₁₀H₂₁ 89 1-methylnonyl 90 2-methylnonyl 91 3-methylnonyl 92 4-methylnonyl 93 5-methylnonyl 94 1-ethyloctyl 95 2-ethyloctyl 96 3-ethyloctyl 97 4-ethyloctyl 98 5-ethyloctyl 99 6-ethyloctyl 100 7-ethyloctyl 101 8-ethyloctyl 102 1,1-dimethyloctyl 103 1,2-dimethyloctyl 104 1,3-dimethyloctyl 105 1,4-dimethyloctyl 106 1,5-dimethyloctyl 107 1,6-dimethyloctyl 108 1,7-dimethyloctyl 109 c-C₁₀H₁₉ 110 n-C₁₁H₂₃ 111 1-methyldecyl 112 1-ethylnonyl 113 1,1-dimethylnonyl 114 n-dodecyl 115 1-methylundecyl 116 1-ethyldecyl 117 1,1-dimethyldecyl 118 1-propylnonyl 119 n-tridecyl 120 1-methyldodecyl 121 1-ethylundecyl 122 1,1-dimethylundecyl 123 n-tetradecyl 124 1-methyltridecyl 125 1-ethyldodecyl 126 1,1-dimethyldodecyl 127 n-pentadecyl 128 CH₂CH═CH₂ 129 CH₂C≡CH 130 CH₂C(CH₃)═CH₂ 131 CH(CH₃)CH═CH₂ 132 CH(CH₃)C≡CH 133 C(CH₃)₂CH═CH₂ 134 C(CH₃)₂C≡CH 135 CH₂CH═CH—CH₃ 136 CH₂—C≡C—CH₃ 137 (CH₂)₂CH═CH—CH₃ 138 (CH₂)₂C≡C—CH₃ 139 (CH₂)₃CH═CH₂ 140 (CH₂)₃C≡CH 141 (CH₂)₃CH═CHCH₃ 142 (CH₂)₃C≡C—CH₃ 143 CH₂CH₂Cl 144 CH₂CH₂Br 145 (CH₂)₃Cl 146 CH(CH₃)CH₂Cl 147 (CH₂)₂F 148 (CH₂)₃F 149 (CH₂)₄Cl 150 (CH₂)₅Cl 151 C(CH₃)₂CH₂Cl 152 CH₂CH₂OCH₃ 153 CH(CH₃)CH₂OCH₃ 154 C(CH₃)₂CH₂OCH₃ 155 (CH₂)₃OCH₃ 156 (CH₂)₂OC₂H₅ 157 CH(CH₃)CH₂OC₂H₅ 158 CH₂CH₂SCH₃ 159 CH(CH₃)CH₂SCH₃ 160 C(CH₃)₂CH₂SCH₃ 161 (CH₂)₂SC₂H₅ 162 CH(CH₃)CH₂SC₂H₅ 163 CH₂CH₂S(O)CH₃ 164 CH₂CH₂SO₂CH₃ 165 CH₂CH₂S(O)C₂H₅ 166 CH₂CH₂SO₂C₂H₅ 167 CH₂CH₂OCH₂CH₂OCH₃ 168 CH₂CH₂OCH₂CH₂OC₂H₅ 169 CH(CH₃)CH₂OCH₂CH₂OCH₃ 170 CH₂-c-C₃H₅ 171 CH₂-c-C₄H₇ 172 CH₂-c-C₅H₉ 173 CH₂-c-C₆H₁₁ 174 CH₂CO₂H 175 CH(CH₃)CO₂H 176 (CH₂)₂CO₂H 177 CH₂CO₂CH₃ 178 CH(CH₃)CO₂CH₃ 179 CH₂CH₂—O—CH₂CH═CH₂ 180 CH₂CH₂O—CH₂C≡CH 181 CH₂CH₂O—CH₂CH₂Cl 182 C(CH₃)₂CO₂CH₂CH═CH₂ 183 C(CH₃)₂CO₂CH₂C≡CH 184 (CH₂)₂O-c-C₃H₅ 185 (CH₂)₂O-c-C₅H₇ 186 (CH₂)₂O-CH₂-CH═CHCl 187 (CH₂)₂S-CH₂CH═CHCl 188 (CH₂)₂S-CH₂CH═CH₂ 189 (CH₂)₂S-CH₂C≡CH 190 (CH₂)₂CN 191 (CH₂)₃CN 192 CH(CH₃)CN 193 (CH₂)₄CN 194 (CH₂)₅CN 195 (CH₂)₆CN 196 CH₂C(O)H 197 CH₂C(O)CH₃ 198 CH₂C(O)C₂H₅ 199 CH₂C(O)CH₂OCH₃ 200 CH₂C(O)(CH₂)₂OCH₃ 201 CH₂C(O)CH₂CN 202 CH₂C(O)CH═CH₂ 203 CH₂P(O)(OCH₃)₂ 204 (CH₂)₂P(O)(OCH₃)₂ 205 CH₂P(S)(OCH₃)₂ 206 CH₂C(O)NHCH₃ 207 CH₂C(O)N(CH₃)₂ 208 (CH₂)₂C(O)N(CH₃)₂ 209 CH₂OC₆H₅ 210 CH₂O-p-Cl-phenyl 211 CH₂O-p-tolyl 212 (CH₂)₂O—C₆H₅ 213 (CH₂)₂O-p-Cl-phenyl 214 (CH₂)₂O-p-tolyl 215 C₆H₅ 216 p-Cl-phenyl 217 m-Cl-phenyl 218 o-Cl-phenyl 219 o-tolyl 220 m-tolyl 221 p-tolyl 222 p-CH₃O-phenyl 223 m-CH₃O-phenyl 224 o-CH₃O-phenyl 225 2,3-dichlorophenyl 226 2,4-dichlorophenyl 227 3-CH₃-4-chlorophenyl 228 3-CH₃O-4-chlorophenyl 229 2-CF₃-phenyl 230 3-CF₃-phenyl 231 4-CF₃-phenyl 232 2-Cl-4-CF₃-phenyl 233 3-Cl-4-CH₃O-phenyl 234 3-F₂CH-o-phenyl 235 4-F₂CH-o-phenyl 236 2-NO₂-phenyl 237 3-NO₂-phenyl 238 4-NO₂-phenyl 239 2-CN-phenyl 240 3-CN-phenyl 241 4-CN-phenyl 242 2-CH₃OC(O)-phenyl 243 3-CH₃OC(O)-phenyl 244 4-CH₃OC(O)-phenyl 245 3-CH₃O—C(O)CH₂O-phenyl 246 3-CH₃O—C(O)CH(CH₃)O-phenyl 247 4-CH₃O—C(O)CH₂O-phenyl 248 4-CH₃O—C(O)C(CH₃)₂O-phenyl 249 2-pyridyl 250 3-pyridyl 251 4-pyridyl 252 1-naphthyl 253 2-naphthyl 254 2-chloro-1-naphthyl 255 3-chloro-1-naphthyl 256 4-chloro-1-naphthyl 257 5-chloro-1-naphthyl 258 2-chloro-4-nitro-1-naphthyl 259 2-methyl-4-nitro-1-naphthyl 260 5-chloro-8-methyl-1-naphthyl 261 2-quinolyl 262 3-quinolyl 263 4-quinolyl 264 5-quinolyl 265 8-quinolyl 266 2-quinazolyl 267 4-quinazolyl 268 1-quinoxalyl 269 1-methylindolyl-2 270 1-methylindolyl-3 271 1-methylbenzimidazolyl-2 272 benzofuran-2-yl 273 benzofuran-3-yl 274 benzofuran-4-yl 275 benzofuran-5-yl 276 benzofuran-6-yl 277 3-methylbenzofuran-5-yl 278 benzothienyl-2 279 benzothienyl-3 280 benzoxazolyl-3 281 benzoxazolyl-4 282 benzoxazolyl-5 283 benzothiazolyl-3 284 benzothiazolyl-4 285 benzothiazolyl-5 286 benzyl 287 2-CH₃-benzyl 288 3-CH₃-benzyl 289 4-CH₃-benzyl 290 2-Cl-benzyl 291 3-Cl-benzyl 292 4-Cl-benzyl 293 2,3-dichlorobenzyl 294 2,4-dichlorobenzyl 295 2-CH₃-4-Cl-benzyl 296 2-Cl-4-CH₃-benzyl 297 2,6-Cl₂-4-CH₃-benzyl 298 2-CH₃O-benzyl 299 3-CH₃O-benzyl 300 4-CH₃O-benzyl 301 2-NO₂-benzyl 302 3-NO₂-benzyl 303 4-NO₂-benzyl 304 2-CN-benzyl 305 3-CN-benzyl 306 4-CN-benzyl

In Table 2 “o” denotes ortho, “m” denotes meta, “p” denotes para, indicating the position at the phenyl ring of the substituent listed next.

Very particular preference is also given to the compounds of the formula Ib.2,

in which R³ has the meanings listed in rows 1 to 306 of Table 2.

Very particular preference is furthermore given to the compounds of the formula Ib.3

in which R³ has the meanings given in rows 1 to 306 of Table 2.

Very particular preference is furthermore given to the compounds of the formula Ib.4

in which R³ has the meanings given in rows 1 to 306 of Table 2.

Very particular preference is furthermore given to the compounds of the formula Ib.5

in which R³ has the meanings given in rows 1 to 306 of Table 2.

Very particular preference is furthermore given to the compounds of the formula Ib.6

in which R³ has the meanings given in rows 1 to 306 of Table 2.

Very particular preference is furthermore given to the compounds of the formula Ib.7

in which R³ has the meanings given in rows 1 to 306 of Table 2.

Very particular preference is furthermore given to the compounds of the formula Ib.8

in which R³ has the meanings given in rows 1 to 306 of Table 2.

According to the invention, the perhydrodiazine derivatives of the formula I are prepared by initially reacting a substituted hydrazine of the formula II

in which Z is O or S and R^(A) and m are as defined above with an acid derivative of the formula III

R—G  (III)

in which R is as defined above and G is a nucleophilically displaceable leaving group, or R—G is an isocyanate of the formula R⁵—N═C═X or a ketene of the formula R^(2a)(R^(2b))C═C═X in which X is O or S and R^(2a)(R^(2b))C—H is the radical R², R² and R⁵ being as defined above, and the resulting hydrazine derivative of the formula IV

is, in a second step, cyclized with formaldehyde in the presence of an acid to give the substituted perhydrodiazines of the formula I where Z═O or S. If appropriate, the radical R in the compounds of the formula I can be subsequently derivatized or converted into other radicals R by standard means; and/or in the case that Z═S, the compounds I can be oxidized in a further reaction step to give the sulfoxide Z═SO or the sulfones Z═SO₂.

Examples of suitable nucleophilically displaceable leaving groups are halogen, preferably chlorine or bromine, C₁-C₆-alkoxy such as methoxy, ethoxy, n-propoxy, n-butoxy, C₁-C₄-haloalkoxy such as trichloromethoxy, trifluoromethoxy, pentafluoroethoxy, N-bonded heterocyclyl such as imidazolyl, C₁-C₆-alkylcarbonyloxy (or C₁-C₆-alkanoate) such as acetate, propionate, n-butyrate, isobutyrate, pivalate and caproate, C₁-C₆-haloalkylcarbonyloxy such as mono-, di- and trichloroacetate, C₁-C₆-alkylsulfonyloxy such as methylsulfonyloxy,

C₁-C₆-haloalkylsulfonyloxy such as trifluoromethylsulfonyloxy, phenylsulfonyloxy, where the phenyl radical may, if appropriate, be mono- or disubstituted by halogen or C₁-C₆-alkyl, such as phenylsulfonyloxy, p-toluenesulfonyloxy and p-Cl-phenylsulfonyloxy, N-bonded nitrogen-C₅-C₆-heterocyclyl, such as N-imidazolyl.

Preferred leaving groups are halogen, in particular chlorine or bromine, and furthermore acetate or trifluoroacetate, in particular if R is a group C(O)OR³, C(S)OR³, C(S)SR³, C(O)SR³, P(O)R¹(OR¹), P(O)(OR¹)₂, S(O)₂R² or SO₂HNR¹.

According to the invention, it is also possible to prepare the compounds of the formula I by reacting, in the first reaction step, a substituted hydrazine with an isocyanate or an isothiocyanate of the formula R′—N═C═X, in which R′ is R⁵, or R′ is a group R⁶—W where W═CO₂, S(O)₂ or S(O)₂O. R⁵ and R⁶ are here as defined above. In the resulting hydrazines of the formula IV, R has then the meanings C(O)NR⁴R⁵ where R⁴═H, C(S)NR⁴R⁵ where R⁴═H, C(O)NHCO₂R⁶, C(O)NHS(O)₂R⁶ or C(O)NHS(O)₂OR⁶.

According to the invention, it is also possible to prepare the compounds of the formula I in which R is C(O)R² by reacting the substituted hydrazines with a ketene of the formula (R^(2a))(R^(2b))C═C═O. In this case, R is a radical C(O)R² where R²═HC(R^(2a))(R^(2b))

In a second reaction step, the hydrazides of the formula (IV) are then reacted with formaldehyde to give the 1-oxa-3,4-diazines or 1-thia-3,4-diazines of the formula I according to the invention here Z═O or S. The reaction can be carried out both using formaldehyde or a compound which releases formaldehyde under acidic conditions, such as paraformaldehyde or 1,3,5-trioxane, in the presence of an acid.

However, it is also possible to react the hydrazides IV with formaldehyde to give the compounds of the formula IVa which are then cyclized to give the 1-oxa- or 1-thiadiazines according to the invention.

The cyclization is usually carried out under acidic conditions.

The reaction described in the scheme below is an example for the preparation of the compound I where, starting from 2-hydrazinoethanol and methyl chloroformate as acid derivative, firstly N-amino-N-methoxycarbonyl-2-hydrazinoethanol is prepared, which is cyclized in a subsequent reaction with formaldehyde to give tetrahydro-4-methoxycarbonyl-4H-1-oxa-3,4-diazine.

Preferred embodiments of the process are mentioned below:

The first reaction step is explained in more detail below: the reaction of the hydrazinoethanol/thiols II with the compounds of the formula III is advantageously carried out in the presence of a solvent at from −30 to 100° C., preferably from −10 to 80° C., particularly preferably from 0 to 60° C.

The solvents used for these reactions are—depending on the temperature range—hydrocarbons, such as pentane, hexane, cyclopentane, cyclohexane, toluene, xylene, chlorinated hydrocarbons, such as methylene chloride, chloroform, 1,2-dichloroethane, 1,1,2,2-tetrachloroethane, chlorobenzene, 1,2-, 1,3- or 1,4-dichlorobenzene, ethers, such as 1,4-dioxane, anisol, glycol ethers such as dimethyl glycol ether, diethyl glycol ether, diethylene glycol dimethyl ether, esters such as ethyl acetate, propyl acetate, methylisobutyrate, isobutylacetate, carboxamides, such as DMF, N-methylpyrrolidone, nitrated hydrocarbons, such as nitrobenzene, ureas, such as tetraethyl urea, tetrabutyl urea, dimethylethylene urea, dimethylpropylene urea, sulfoxides such as dimethyl sulfoxide, sulfones such as dimethyl sulfone, diethyl sulfone, tetramethylene sulfone, nitriles, such as acetonitrile, propionitrile, butyronitrile or isobutyronitrile; water or else mixtures of individual solvents.

The molar ratios in which the starting materials II and III are reacted with one another are generally from 0.9 to 1.2, preferably 0.95 to 1.1, particularly preferably 0.98 to 1.04, for the ratio of acid derivative of the formula III to hydrazinoethanol/thiol II.

The first reaction step is advantageously carried out under neutral conditions. If an acidic reaction product is formed in the reaction, for example hydrogen halide if G in the formula III is halogen, this is removed by addition of basic compounds, for example alkali metal or alkaline earth metal hydroxides or bicarbonates or carbonates. However, the reaction can also be carried out in the presence of an organic base, for example triethylamine, tri-n-propylamine, N-ethyldiisopropylamine, pyridine, α-, β-, γ-picoline, 2,4-, 2,6-lutidine, N-methylpyrrolidine, dimethylaniline, N,N-dimethylcyclohexylamine, quinoline or acridine.

Finally, the reaction can also be carried out in an aqueous two-phase system, preferably in the presence of phase-transfer catalysts, such as quaternary ammonium or phosphonium salts. The reaction conditions described in EP-A 556737 are suitable for the two-phase reaction.

The phase-transfer catalysts used can be quaternary ammonium or phosphonium salts. Suitable compounds which may be mentioned are: tetraalkyl(C₁-C₁₈)ammonium chlorides, bromides or fluorides, N-benzyltrialkyl(C₁-C₁₈)ammonium chlorides, bromides or fluorides, tetraalkyl(C₁-C₁₈)phosphonium chlorides or bromides, tetraphenylphosphonium chloride or -bromide, (phenyl)_(o)(alkyl(C₁-C₁₈)_(p)-phosphonium chlorides or bromides, where o=1 to 3, p=3 to 1 and o+p=4. Particular preference is given to tetraethylammonium chloride and N-benzyltriethylammonium chloride. The amount of phase-transfer catalyst is generally up to 20% by weight, preferably between 1 and 15% by weight. and particularly preferably between 2 and 8% by weight, based on the hydrazinoethanol/thiol II.

Advantageously, the acid derivative III is added, at 0 to 60° C. and over a period of 0.25 to 2 hours, to a mixture of the hydrazinoethanol/thiol II and the base in one of the abovementioned solvents, and stirring at 0 to 60° C. is continued for 0.5 to 16 hours, preferably 2 to 8 hours, for the reaction to go to completion.

If an aqueous two-phase system is used, the starting materials II and III can be added with stirring, in any order, to a mixture of the phase-transfer catalyst in the two phases, and the reaction can then be completed in the temperature range mentioned by adding base.

If the compound of the formula III is an isocyanate isothiocyanate or a ketene, addition of a base can be dispensed with. The reaction is in this case preferably carried out under anhydrous conditions.

The reaction can be carried out under atmospheric pressure or superatmospheric pressure, continuously or batchwise.

For work-up, any precipitated salts are separated off, or their removal is completed by addition of nonpolar solvents, and the hydrazides IV are thus enriched in the filtrate.

The second reaction step is explained below: the hydrazides IV are subsequently reacted, advantageously under acidic conditions, with a formaldehyde solution or paraformaldehyde in one of the abovementioned solvents.

For the subsequent step, advantageously 0.9 to 1.2, preferably 0.95 to 1.1, particularly preferably 0.98 to 1.04, molar equivalents of formaldehyde or paraformaldehyde are employed per mole of hydrazide derivative IV. The concentration of the starting materials in the solvent is 0.1 to 5 mol/l, preferably 0.2 to 2 mol/l.

The acid used can be an aromatic sulfonic acid, for example benzenesulfonic acid, p-chloro- or p-toluenesulfonic acid, an aliphatic sulfonic acid, such as methane sulfonic acid, trifluoromethane sulfonic acid, ethanesulfonic acid and n-propylsulfonic acid, a sulfaminic acid, such as methylsulfaminic acid, ethylsulfaminic acid or isopropylsulfaminic acid, an aliphatic carboxylic acid, such as acetic acid, trifluoroacetic acid, propionic acid, butyric acid or isobutyric acid, or an inorganic acid, such as hydrochloric acid, sulfuric acid, nitric acid or boric acid. Advantageously, it is also possible to use an acid such as acetic acid or propionic acid directly as reaction medium. The acid catalyst is advantageously employed in the amount from 1 to 20 mol %, preferably 3 to 15 mol %, particularly preferably 5 to 10 mol %, of acid per mole of hydrazide IV.

Preferably, a formaldehyde solution or paraformaldehyde is added over a period of 2 to 60 min to a mixture of hydrazide IV and the acid catalyst in one of the abovementioned solvents a 0 to 100° C., advantageously 10 to 80° C., particularly preferably 20 to 50° C., and stirring is continued at 40 to 50° C. for 10 to 50 hours, preferably 15 to 30 hours, to bring the reaction to completion.

If an aqueous formaldehyde solution is used, the water is advantageously removed, for example using a water separator.

However, it is also possible to add the acidic catalyst to a mixture of hydrazide IV and paraformaldehyde in one of the abovementioned solvents, and then to complete the reaction as described.

The reaction can be carried out under atmospheric pressure or under superatmospheric pressure, continuously or batchwise.

The oxidation of the perhydrodiazines I where Z═S to the sulfoxides, which follows, if appropriate, is preferably carried out using hydrogen peroxide, the sulfoxides being obtained with approximately equivalent amounts of oxidant, and the sulfones being obtained with about double the molar quantities.

The oxidation with hydrogen peroxide can be catalyzed by suitable metal compounds, for example transition metal oxides, such as vanadium pentoxide, sodium tungstate, potassium dichromate, iron oxide tungstate, sodium tungstate/molybdic acid, osmic acid, titanium trichloride, selenium dioxide, phenylselenic acid, vanadyl 2,4-pentane dionate. The catalysts are generally employed in an amount of from 0.5 to 10%, but it is also possible to employ stoichiometric amounts because the inorganic catalysts can easily be filtered off and recovered.

Solvents which are suitable for the oxidation with hydrogen peroxide are, for example, water, acetonitrile, alcohols, such as methanol, ethanol, isopropanol, tert-butanol, chlorinated hydrocarbons, such as methylene chloride, 1,1,2,2-tetrachloroethane, or ketones, such as acetone or methyl ethyl ketone.

In addition to hydrogen peroxide, it is also possible to use, as oxidizing agents, peracids, such as perbenzoic acid, monoperphthalic acid or 3-chloroperbenzoic acid. The reaction with peracids is expediently carried out in chlorinated hydrocarbons, such as methylene chloride or 1,2-dichloroethane.

Also very suitable for oxidizing the thiols to sulfoxides or sulfones are chorine and bromine. This oxidation is expediently carried out in polar solvents, such as water, acetonitrile, dioxane, or in two-phase systems, such as aqueous potassium bicarbonate solution/dichloromethane, and also acetic acid. It is furthermore possible to employ as source of active halogen tert-butyl hypochlorite, hypochlorous and hypobromous acids, their salts, and also N-halo compounds, such as N-bromo- and N-chlorosuccinimide or else sulfuryl chloride.

Also suitable for the oxidation is photosensitized oxygen transfer, in which case the photosensitizers used are usually organic dyes, for example porphyrines, such as tetraphenylphorphyrine, chlorophyll, protoporphyrine, xanthene dyes, such as rose Bengal, or phenothiazine dyes, such as methylene blue.

Suitable inert solvents are hydrocarbons, such as pentane, hexane, heptane, cyclohexane, chlorinated hydrocarbons, such as methylenechloride, 1,2-dichloroethane, 1,1,2,2-tetrachloroethane, alcohols, such as methanol, ethanol, n-propanol or isopropanol, ketones, such as acetone, methyl ethyl ketone, polar aprotic solvents such as acetonitrile, propionitrile, or aromatic hydrocarbons, such as benzene, toluene, chlorobenzene or xylene. In place of oxygen, it is also possible to use ozone in the abovementioned solvents, plus ether, 1,4-dioxane or THF.

Besides photosensitization, catalysts are also advisable for oxidation with oxygen, for example oxides and sulfides of nickel, copper, aluminum, tungsten, chromium, vanadium, ruthenium, titanium, manganese, molybdenum, magnesium and iron.

Either the sulfoxides I B or their sulfones I C are obtained, depending on the stoichiometry of the oxidizing agents used. The molar ratios in which the starting compounds are reacted with one another are generally 0.9 to 1.8, preferably 1.05 to 1.3, for the ratio of thiadiazine I A to oxidizing agent in the case of the oxidation to the sulfoxide and generally 1.9 to 3.5, preferably 2.05 to 2.9, in the case of oxidation to the sulfone.

The concentration of the starting materials in the solvent is generally 0.1 to 5 mol/l, preferably 0.2 to 2 mol/l.

It is advantageous to initially charge the 1-thiadiazine of the formula I where Z═S or the sulfoxide, if appropriate together with one of the abovementioned catalysts, in one of the abovementioned solvents, and then to add the oxidizing agent over the course of 0.25 to 20 hours with stirring. The addition and the reaction temperature depends on the optimum efficiency of the oxidizing agent in question and on avoiding side-reactions. If photosensitized oxygen is used, the reaction is generally carried out at from −20 to 80° C.; however, if metal catalysis is employed, the reaction is generally carried out at from 50 to 140° C., and if ozone is used, the reaction is generally carried out at from −78 to 60° C. Owing to the limited solubility of the oxygen derivatives, they are preferably introduced continuously into the reaction mixture over a relatively long period of time (up to 20 h) until the oxidation on the sulfoxide or sulfone stage has been completed. Liquid or easily soluble oxidizing agents, such as hydrogen peroxide, hypochlorous or hypobromous acid, tert-butyl hypochlorite, chlorite or bromine, furthermore N-chloro or N-bromosuccinimide, can be added to the reaction mixture of the thiadiazine or thiadiazine sulfoxide over shorter periods of time, such as 0.25 to 6 h, depending on the exothermic character of the reaction, and the reaction is ended after a further 1 to 60 h. Preference is furthermore given to adding the liquid or dissolved oxidizing agent gradually. In the case of hydrogen peroxide, the reaction is generally carried out at from 0 to 90° C., with tert-butyl hypochlorite, the reaction is generally carried out at from −78 to 30° C. and with N-halo compounds generally from 0 to 30° C. In the case of chlorine or bromine, a reaction temperature of from 0 to 40° C. is recommended.

The oxidations can be carried out under atmospheric or superatmospheric pressure, continuously or batchwise.

The multi-step reaction can advantageously also be carried out as a one-part process, where the thiadiazines I (Z═S) are converted directly, without isolation and purification, into the sulfoxides I (Z═SO) or the sulfones I (Z═SO₂). Accordingly, the reaction product Ia is, if appropriate, allowed to cool to from 90 to 20° C., a solvent, for example methylene chloride and/or water, is added, if appropriate, and the oxidizing agent is then added at the rate of its consumption. Particularly preferred oxidizing agents are hydrogen peroxide and sodium hypochlorite.

For work-up of the oxidation mixture, the end products I are generally taken up in a water-immiscible solvent, acidic impurities and/or oxidizing agents are extracted using dilute alkali or water, the mixture is dried and the solvent is removed under reduced pressure.

In principle, the substituted perhydrodiazines I can be prepared by the synthesis process according to the invention mentioned above. For economical or technical reasons, however, it may be more expedient to prepare some of the compounds I from similar substituted perhydrodiazines which differ in the meaning of one radical.

The work-up of the reaction mixtures is generally carried out by methods known per se, for example by dilution of the reaction solution with water and subsequent isolation of the product by filtration, crystallization or solvent extraction, or by removing the solvent, partitioning the residue in a mixture of water and suitable organic solvent and work-up of the organic phase to afford the product.

The compounds of the formula I according to the invention are obtainable in good yields. They can also be prepared on a relatively large scale. Accordingly, they are particularly suitable for use as starting materials for the preparation of compounds having a 1-hetero-3,4-diazine structure of the formula

in which R, Z, R^(A) and m are as defined above and R^(x) is any organic radical.

It has now been found that compounds of the formula V

in which R, R^(A), Z and m are as defined in claims 1 to 4,

X is O or S, and

Q is a C₆-C₁₄-aromatic radical which is at least monosubstituted and/or attached via two adjacent carbon atoms to a saturated or unsaturated 4- to 7-membered cycle which, in addition to the carbon ring members, may contain, if desired, one, two or three of the following members: —O—, —S—, —S(O)₂— —N═, —NH— or —N(C₁-C₆-alkyl)—;

have particularly good herbicidal activity. Such compounds are novel, and they form part of the subject matter of a further patent application.

It has been found that the compounds of the formula V can be prepared starting with the compounds of the formula I by reaction with isocyanates or isothiocyanates of the formula VI

Q—N═C═X

in which Q and X are as defined above.

Accordingly, the present invention also relates to a process for preparing compounds of the formula V (substituted ureas) which comprises reacting the compounds of the formula I defined above with an isocyanate or isocyothianate of the formula VI.

With a view to the herbicidal activity of the substituted ureas of the formula V, Q is, for example, a radical Q1 to Q6:

in which

Y and Y′ independently of one another are O or S;

T is a chemical bond or O;

U is a chemical bond, C₁-C₄-alkylene, O, S, SO or SO₂;

and the radicals R⁸ to R^(12′)are as defined below:

R⁸ is hydrogen or halogen;

R⁹ C₁-C₆-alkyl, C₁-C₆-haloalkyl, OCH₃, SCH₃, OCHF₂, halogen, cyano or NO₂;

R¹⁰ is hydrogen, hydroxyl, mercapto, cyano, nitro, halogen, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-haloalkyl, C₁-C₆-haloalkoxy, C₁-C₆-haloalkylthio, C₁-C₆-alkoxy-(C₁-C₆-alkyl)carbonyl, C₁-C₆-alkylthio-(C₁-C₆-alkyl)carbonyl, (C₁-C₆-alkyl)iminooxycarbonyl, C₁-C₆-alkoxy-C₁-C₆-alkyl, C₁-C₆-alkoxyamino-C₁-C₆-alkyl, C₁-C₆-alkoxy-C₁-C₆-alkylamino-C₁-C₆-alkyl,

is C₁-C₆-alkoxy, C₁-C₆-alkylthio, C₃-C₆-cycloalkoxy, C₃-C₆-cycloalkylthio, C₂-C₆-alkenyloxy, C₂-C₆-alkenylthio, C₂-C₆-alkynyloxy, C₂-C₆-alkynylthio, (C₁-C₆-alkyl)carbonyloxy, (C₁-C₆-alkyl)carbonylthio, (C₁-C₆-alkoxy)carbonyloxy, (C₂-C₆-alkenyl)carbonyloxy, (C₂-C₆-alkenyl)carbonylthio, (C₂-C₆-alkynyl)carbonyloxy, (C₂-C₆-alkynyl)carbonylthio, C₁-C₆-alkylsulfonyloxy or C₁-C₆-alkylsulfonyl, where each of the 17 last-mentioned radicals may, if desired, carry one, two or three substituents, selected from the group consisting of:

halogen, nitro, cyano, hydroxyl, C₃-C₆-cycloalkyl, C₁-C₆-alkoxy, C₃-C₆-cycloalkoxy, C₃-C₆-alkenyloxy, C₃-C₆-alkynyloxy, C₁-C₆-alkoxy-C₁-C₆-alkoxy, C₁-C₆-alkylthio, C₁-C₆-alkylsulfinyl, C₁-C₆-alkylsulfonyl, C₁-C₆-alkylideneaminoxy, oxo, ═N—OR¹³;

phenyl, phenoxy or phenylsulfonyl, where the three last-mentioned groups may carry one, two or three substituents, selected from the group consisting of halogen, nitro cyano, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy and (C₁-C₆-alkoxy)carbonyl;

CO—R¹⁴, —CO—OR¹⁴, —CO—SR¹⁴, —CO—N(R¹⁴)—R¹⁵, —OCO—R¹⁴, —OCO—OR¹⁴′, —OCO—SR¹⁴′, —OCO—N(R¹⁴)—R¹⁵, —N(R¹⁴)—R¹⁵, and C(R¹ ⁶)═N—OR¹³;

is C(Z¹)—R¹⁷, —C(═NR¹⁸)R¹⁷, C(R¹⁷)(Z²R¹⁹)(Z³R²⁰) C(R¹⁷)═C(R²¹)—CN, C(R¹⁷)═C(R²¹)—CO—R²², —CH(R¹⁷)—CH(R²¹)—COR²², —C(R¹⁷)═C(R²¹)—CH₂—CO—R²², —C(R¹⁷)═C(R²¹)—C(R²³)═C(R²⁴)—CO—R²², —C(R¹⁷)═C(R²¹)—CH₂—CH(R²⁵)—CO—R²², —CO—OR²⁶, —CO—SR²⁶, —CON(R²⁶)—OR¹³, —C≡C—CO—NHOR¹³, —C≡C—CO—N(R²⁶)—OR¹³, —C≡C—CS—NH—OR¹³, —C═C—CS—N(R²⁶)—OR¹³, —C(R¹⁷)═C(R²¹)—CO—NHOR¹³, —C(R¹⁷)═C(R²¹)—CO—N(R²⁶)—OR¹³, —C(R¹⁷)═C(R²¹)—CS—NHOR¹³, —C(R¹⁷)═C(R²¹)—CS—N(R²⁶)—OR¹³, —C(R¹⁷)═C(R²¹)—C(R¹⁶)═N—OR¹³, C(R¹⁶)═N—OR¹³, —C≡C—C(R¹⁶)═NOR¹³, C(Z²R¹⁹)(Z³R²⁰)—OR²⁶, —C(Z²R¹⁹)(Z²R²⁰)SR²⁶, C(Z²R¹⁹)(Z³R²⁰)—N(R²⁷)R²⁸, —N(R²⁷)—R²⁸, —CO—N(R²⁷)—R²⁸ or C(R¹⁷)═C(R²¹)CO—N(R²⁷)R²⁸; where Z¹, Z² and Z³ independently of one another are oxygen or sulfur;

R¹¹ is hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₃-alkoxy-C₁-C₃-alkyl, C₃-C₆-alkenyl, C₁-C₃-alkoxy-C₃-C₆-alkenyl, C₃-C₆-haloalkenyl, C₃-C₆-alkynyl, C₁-C₃-alkoxy-C₃-C₆-alkynyl, C₃-C₆-haloalkynyl, C₃-C₇-cycloalkyl, 3- to 7-membered saturated heterocyclyl, where each cycloalkyl and each heterocyclyl ring may contain a carbonyl or thiocarbonyl ring member and where each cycloalkyl and heterocyclyl ring may be unsubstituted or may carry one, two, three or four substituents, selected from the group consisting of cyano, nitro, amino, hydroxyl, halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-cyanoalkyl, C₁-C₄-hydroxyalkyl, C₁-C₄-aminoalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio, C₁-C₄-alkylsulfinyl, C₁-C₄-alkylsulfonyl, C₁-C₄-haloalkylsulfonyl, (C₁-C₄-alkoxy)carbonyl, (C₁-C₄-alkyl)carbonyl, (C₁-C₄-haloalkyl)carbonyl, (C₁-C₄-alkyl)carbonyloxy, (C₁-C₄-haloalkyl)carbonyloxy, di(C₁-C₄-alkyl)amino, C₃-C₆-alkenyl, C₃-C₆-alkynyl, C₃-C₄-alkenyloxy, C₃-C₄-alkenylthio, C₃-C₄-alkynyloxy and C₃-C₄-alkynylthio;

R^(11′) is hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₃-alkoxy-C₁-C₃-alkyl, C₂-C₆-cyanoalkyl, C₃-C₆-alkenyl, C₃-C₆-alkynyl;

R¹² is hydrogen, C₁-C₃-alkyl, C₁-C₃-haloalkyl or halogen;

R^(12′) is hydrogen, C₁-C₃-alkyl, C₁-C₃-haloalkyl; or

R¹² and R^(12′) together are C═O.

The variables R¹³ to R³⁰ listed under R¹⁰ have, for example, the following meanings:

R¹³ is hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₃-C₆-cycloalkyl, C₃-C₆-alkenyl, C₃-C₆-alkynyl, hydroxy-C₁-C₆-alkyl, C₁-C₆-alkoxy-C₁-C₆-alkyl, C₁-C₆-alkylthio-C₁-C₆-alkyl, cyano-C₁-C₆-alkyl, (C₁-C₆-alkyl)carbonyl-C₁-C₆-alkyl, (C₁-C₆-alkoxy)carbonyl-C₁-C₆-alkyl, (C₁-C₆-alkoxy)carbonyl-C₂-C₆-alkenyl, (C₁-C₆-alkyl)carbonyloxy-C₁-C₆-alkyl or phenyl-C₁-C₆-alkyl, in which the phenyl ring may, if desired, carry one, two or three substituents, selected from the group consisting of cyano, nitro, halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy and (C₁-C₆-alkoxy)carbonyl;

R¹⁴ is hydrogen, C₁-C₆-alkyl, C₃-C₆-cycloalkyl, C₃-C₆-alkenyl, C₃-C₆-alkynyl, C₁-C₆-alkoxy-C₁-C₆-alkyl, (C₁-C₆-alkoxy)carbonyl-C₁-C₆-alkyl, (C₃-C₆-alkenyloxy)carbonyl-C₁-C₆-alkyl, phenyl or phenyl-C₁-C₆-alkyl, where the phenyl ring of the two last-mentioned groups may be unsubstituted or may carry one, two or three radicals, selected from the group consisting of halogen, nitro, cyano, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy and (C₁-C₆-alkyl)carbonyl;

R^(14′) has the meanings of R¹⁴ with the exception of hydrogen;

R¹⁵ is hydrogen, hydroxyl, C₁-C₆-alkyl C₃-C₆-cycloalkyl, C₁-C₆-alkoxy, (C₁-C₆-alkoxy)carbonyl-C₁-C₆-alkoxy, C₃-C₆-alkenyl or C₃-C₆-alkenyloxy;

R¹⁶ is hydrogen, halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₃-C₆-alkenyloxy, C₃-C₆-alkynyloxy, C₁-C₆-alkylthio, C₁-C₆-haloalkylthio, (C₁-C₆-alkyl)carbonyloxy, (C₁-C₆-haloalkyl)carbonyloxy, C₁-C₆-alkylsulfonyloxy or C₁-C₆-haloalkylsulfonyloxy, where the 12 last-mentioned radicals may carry one of the following substituents: hydroxyl, cyano, hydroxycarbonyl, C₁-C₆-alkoxy, C₁-C₆-alkylthio, (C₁-C₆-alkyl)carbonyl, (C₁-C₆-alkoxy)carbonyl, (C₁-C₆-alkyl)aminocarbonyl, di(C₁-C₆-alkyl)aminocarbonyl, (C₁-C₆-alkyl)carbonyloxy, C₁-C₆-alkoxy-(C₁-C₆-alkyl)aminocarbonyl;

is (C₁-C₆-alkyl)carbonyl, (C₁-C₆-haloalkyl)carbonyl, (C₁-C₆-alkoxy)carbonyl, (C₁-C₆-alkoxy)carbonyloxy, (C₁-C₆-alkyl)carbonylthio, (C₁-C₆-haloalkyl)carbonylthio, (C₁-C₆-alkoxy)carbonylthio, C₂-C₆-alkenyl, (C₂-C₆-alkenyl)carbonyloxy, C₂-C₆-alkenylthio, C₃-C₆-alkynyl, C₃-C₆-alkynyloxy, C₃-C₆-alkynylthio, (C₂-C₆-alkynyl)carbonyloxy, C₃-C₆-alkynylsulfonyoxy, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkyloxy, C₃-C₆-cycloalkylthio, (C₃-C₆-cycloalkyl)carbonyloxy, C₃-C₆-cycloalkylsulfonyloxy;

is phenyl, phenoxy, phenylthio, benzoyloxy, phenylsulfonyloxy, phenyl-C₁-C₆-alkyl, phenyl-C₁-C₆-alkoxy, phenyl-C₁-C₆-alkylthio, phenyl-(C₁-C₆-alkyl)carbonyloxy or phenyl-(C₁-C₆-alkyl)sulfonyloxy, where the phenyl rings of the 10 last-mentioned radicals may be unsubstituted or may for their part carry one to three substituents, in each case selected from the group consisting of cyano, nitro, halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy and (C₁-C₆-alkoxy)carbonyl;

R¹⁷ is hydrogen, cyano, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl, C₁-C₆-alkoxy-C₁-C₆-alkyl or (C₁-C₆-alkoxy)carbonyl;

R¹⁸ is hydrogen, hydroxyl, C₁-C₆-alkyl, C₃-C₆-alkenyl, C₃-C₆-alkynyl, C₃-C₆-cycloalkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy-C₁-C₆-alkyl, C₁-C₆-alkoxy, C₃-C₆-alkenyloxy, C₃-C₆-alkynyloxy, C₃-C₆-cycloalkoxy, C₅-C₇-cycloalkenyloxy, C₁-C₆-haloalkoxy, C₃-C₆-haloalkenyloxy, hydroxy-C₁-C₆-alkoxy, cyano-C₁-C₆-alkoxy, C₃-C₆-cycloalkyl-C₁-C₆-alkoxy, C₁-C₆-alkoxy-C₁-C₆-alkoxy, C₁-C₆-alkoxy-C₃-C₆-alkenyloxy, (C₁-C₆-alkyl)carbonyloxy, (C₁-C₆-haloalkyl)carbonyloxy, (C₁-C₆-alkyl)carbamoyloxy, (C₁-C₆-haloalkyl)carbamoyloxy, (C₁-C₆-alkyl)carbonyl-C₁-C₆-alkyl, (C₁-C₆-alkyl)carbonyl-C₁-C₆-alkoxy, (C₁-C₆-alkoxy)carbonyl-C₁-C₆-alkyl, (C₁-C₆-alkoxy)carbonyl-C₁-C₆-alkoxy, C₁-C₆-alkylthio-C₁-C₆-alkoxy, di(C₁-C₆-alkyl)amino-C₁-C₆-alkoxy, —N(R²⁹)R³⁰, phenyl, which for its part may carry one, two or three substituents, in each case selected from the group consisting of cyano, nitro, halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₂-C₆-alkenyl, C₁-C₆-alkoxy and (C₁-C₆-alkoxy)carbonyl;

is phenyl-C₁-C₆-alkoxy, phenyl-C₁-C₆-alkyl, phenyl-C₃-C₆-alkenyloxy or phenyl-C₃-C₆-alkynyloxy, where in each case one or two methylene groups of the carbon chains in the four last-mentioned groups may be replaced by —O—, —S—, or —N(C₁-C₆-alkyl)—, and where the phenyl rings in the four last-mentioned groups may be unsubstituted or may for their part carry one to three substituents, selected from the group consisting of cyano, nitrogen, halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₂-C₆-alkenyl, C₁-C₆-alkoxy and (C₁-C₆-alkoxy)carbonyl; is C₃-C₇-heterocyclyl, C₃-C₇-heterocyclyl-C₁-C₆-alkyl, C₃-C₇-heterocyclyl-C₁-C₆-alkoxy, C₃-C₇-heterocyclyl-C₃-C₆-alkenyloxy or C₃-C₇-heterocyclyl-C₃-C₆-alkynyloxy, where in each case one or two methylene groups of the carbon chains in the four last-mentioned groups may be replaced by —O—, —S—or —N(C₁-C₆-alkyl)— and where each heterocycle may be saturated, unsaturated or aromatic and is either unsubstituted or for its part carries one to three substituents, selected from the group consisting of cyano, nitro, halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₂-C₆-alkenyl, C₁-C₆-alkoxy and (C₁-C₆-alkoxy)carbonyl;

R¹⁹, R²⁰ independently of one another are C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₃-C₆-alkenyl, C₃-C₆-alkynyl, C₁-C₆-alkoxy-C₁-C₆-alkyl or together are a saturated or unsaturated, 2- to 4-membered carbon chain which may carry one oxo substituent, where one member of this chain which is not adjacent to the variables Z² and Z³ may be replaced by —O—, —S—, —N═, —NH— or —N(C₁-C₆-alkyl)— and where the carbon chain may carry one to three radicals selected from the group consisting of cyano, nitro, amino, halogen, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₁-C₆-alkoxy, C₂-C₆-alkenyloxy, C₂-C₆-alkynyloxy, C₁-C₆-haloalkyl, cyano-C₁-C₆-alkyl, hydroxy-C₁-C₆-alkyl, C₁-C₆-alkoxy-C₁-C₆-alkyl, C₃-C₆-alkenyloxy-C₁-C₆-alkyl, C₃-C₆-alkynyloxy-C₁-C₆-alkyl, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkoxy, carboxyl, (C₁-C₆-alkoxy)carbonyl, (C₁-C₆-alkyl)carbonyloxy-C₁-C₆-alkyl and phenyl; unsubstituted or substituted phenyl where the carbon chain may also be substituted by a fused-on or spiro-linked 3- to 7-membered ring which may contain one or two hetero atoms as ring members, selected from the group consisting of oxygen, sulfur, nitrogen and C₁-C₆-alkyl-substituted nitrogen, and which, for its part, may, if desired, carry one or two of the following substituents: cyano, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₁-C₆-alkoxy, cyano-C₁-C₆-alkyl, C₁-C₆-haloalkyl and (C₁-C₆-alkoxy)carbonyl;

R²¹ is hydrogen, cyano, halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C_(1-C) ₆-alkoxy, (C₁-C₆-alkyl)carbonyl or (C₁-C₆-alkoxy)carbonyl;

R²² is hydrogen, O—R³¹, S—R³¹, C₁-C₆-alkyl, which may carry one or two C₁-C₆-alkoxy substituents, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-haloalkyl, C₃-C₆-cycloalkyl, C₁-C₆-alkylthio-C₁-C₆-alkyl, C₁-C₆-alkyliminooxy, —N(R²⁷)R²⁸ or phenyl, which may be unsubstituted or may carry one to three substituents, in each case selected from the group consisting of cyano, nitro, halogen, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy and (C₁-C₆-alkoxy)carbonyl;

R²³ is hydrogen, cyano, halogen, C₁-C₆-alkyl, C₃-C₆-alkenyl, C₃-C₆-alkynyl, C₁-C₆-alkoxy-C₁-C₆-alkyl, (C₁-C₆-alkyl)carbonyl, (C₁-C₆-alkoxy)carbonyl, —N(R²⁷)R²⁸ or phenyl, which for its part may carry one to three substituents, selected from the group consisting of cyano, nitro, halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₃-C₆-alkenyl, C₁-C₆-alkoxy and (C₁-C₆-alkoxy)carbonyl;

R²⁴ is hydrogen, cyano, halogen, C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkyl, (C₁-C₆-alkyl)carbonyl or (C₁-C₆-alkoxy)carbonyl;

R²⁵ is hydrogen, cyano, C₁-C₆-alkyl or (C₁-C₆-alkoxy)carbonyl;

R²⁶, R³¹ independently of one another are hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₂-C₆-alkenyl or C₂-C₆-alkynyl, where the 4 last-mentioned groups may in each case carry one or two of the following radicals: cyano, halogen, hydroxyl, hydroxycarbonyl, C₁-C₆-alkoxy, C₁-C₆-alkylthio, (C₁-C₆-alkyl)carbonyl, (C₁-C₆-alkoxy)carbonyl, (C₁-C₆-alkyl)carbonyloxy, (C₃-C₆-alkenyloxy)carbonyl;

are (C₁-C₆-haloalkyl)carbonyl, (C₁-C₆-alkoxy)carbonyl, C₁-C₆-alkylaminocarbonyl, di(C₁-C₆-alkyl)aminocarbonyl, C₁-C₆-alkyloximino-C₁-C₆-alkyl, C₃-C₆-cycloalkyl;

are phenyl or phenyl-C₁-C₆-alkyl, where the phenyl rings may be unsubstituted or may for their part carry one to three substituents, in each case selected from the group consisting of cyano, nitro, halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy and (C₁-C₆-alkoxy)carbonyl;

R²⁷, R²⁸, R²⁹, R³⁰ independently of one another are hydrogen, C₁-C₆-alkyl, C₃-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy-C₁-C₆-alkyl, (C₁-C₆-alkyl)carbonyl, (C₁-C₆-alkoxy)carbonyl, (C₁-C₆-alkoxy)carbonyl-C₁-C₆-alkyl,

are (C₁-C₆-alkoxy)carbonyl-C₂-C₆-alkenyl, where the alkenyl chain may additionally carry one to three halogen and/or cyano radicals, are C₁-C₆-alkylsulfonyl, (C₁-C₆-alkoxy)carbonyl-C₁-C₆-alkylsulfonyl, phenyl or phenylsulfonyl, where the phenyl rings of the two last-mentioned radicals may be unsubstituted or for their part may carry one to three substituents, in each case selected from the group consisting of cyano, nitro, halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₃-C₆-alkenyl, C₁-C₆-alkoxy and (C₁-C₆-alkoxy)carbonyl; or

R²⁷ and R²⁸ and/or

R²⁹ and R³⁰ in each case together with the common nitrogen atom are a saturated or unsaturated 4- to 7-membered azo heterocycle, which in addition to carbon ring members, may, if desired, contain one of the following members:

—O—, —S—, —N═, —NH— or —N(C₁-C₆-alkyl)—.

With a view to the use of the substituted ureas of the formula V as herbicides, the variables preferably have the following meanings, in each case on their own or in combination.

Z is O or S;

R^(A) is CO₂R¹, halogen, cyano, OR² or C₁-C₃-alkyl;

Q is Q-1, Q-2 or Q-4;

X, Y and Y′ independently of one another are O or S;

T is a chemical bond or O;

U is a chemical bond, C₁-C₄-alkylene, O or S;

R is C(O)OR³, C(O)SR³, C(S)OR³, C(S)SR³, CHO, CN, C(O)R², C(O)NR⁴R⁵, C(S)NR⁴R⁵, C(O)NHC(O)₂OR⁶, C(O)NHS(O)₂R⁶, C(O)NHS(O)₂OR⁶;

R¹ is hydrogen or C₁-C₃-alkyl;

R² is C₁-C₃-alkyl, C₃-C₆-cycloalkyl, C₃-C₆-alkenyl, C₃-C₆-alkynyl, C₁-C₃-haloalkyl, C₁-C₃-alkoxycarbonyl-C₁-C₃-alkyl, cyano-C₁-C₃-alkyl, benzyl, which may be substituted by halogen, C₁-C₄-alkyl or trifluoromethyl, or

is phenyl, which may be substituted by halogen, C₁-C₄-alkyl, trifluoromethyl or C₁-C₄-alkoxy;

R³ is C₁-C₁₅-alkyl, C₃-C₈-cycloalkyl, C₂-C₁₀-alkenyl, C₃-C₁₀-alkynyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy-C₁-C₆-alkyl, C₁-C₆-alkoxycarbonyl-C₁-C₆-alkyl, C₃-C₆-alkenyloxy-C₁-C₆-alkyl, C₃-C₆-alkynyloxy-C₁-C₆-alkyl, cyano-C₁-C₆-alkyl,

is phenyl or benzyl, which may in each case be mono- to pentasubstituted by halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, amino, C₂-C₄-monoalkylamino, C₁-C₄-dialkylamino, C₁-C₄-alkoxycarbonyl, nitro or cyano;

R⁴ is hydrogen, C₁-C₆-alkyl or C₁-C₆-alkoxy;

R⁵, R⁶ independently of one another are hydrogen, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy-C₁-C₆-alkyl, phenyl or benzyl, which may be mono- to pentasubstituted by halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-dialkylamino, C₁-C₄-alkoxycarbonyl, nitro or cyano; or

R⁴ and R⁵ together with the common nitrogen atom are a saturated or unsaturated 4- to 7-membered azo heterocycle

R⁸ is hydrogen, fluorine or chlorine;

R⁹ is chlorine, trifluoromethyl or cyano;

R¹⁰ is hydrogen, hydroxyl, mercapto, cyano, nitro, halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-haloalkoxy, C₁-C₆-haloalkylthio, C₁-C₆-alkoxy-(C₁-C₆-alkyl)carbonyl, C₁-C₆-alkylthio-(C₁-C₆-alkyl)carbonyl, (C₁-C₆-alkyl)iminooxycarbonyl, C₁-C₆-alkoxy-C₁-C₆-alkyl, C₁-C₆-alkoxyamino-C₁-C₆-alkyl, C₁-C₆-alkoxy-C₁-C₆-alkylamino-C₁-C₆-alkyl,

is C₁-C₆-alkoxy, C₁-C₆-alkylthio, C₃-C₆-cycloalkoxy, C₃-C₆-Cycloalkylthio, C₂-C₆-alkenyloxy, C₂-C₆-alkenylthio, C₂-C₆-alkynyloxy, C₂-C₆-alkynylthio, (C₁-C₆-alkyl)carbonyloxy, (C₁-C₆-alkyl)carbonylthio, (C₁-C₆-alkoxy)carbonyloxy, (C₂-C₆-alkenyl)carbonyloxy, (C₂-C₆-alkenyl)carbonylthio, (C₂-C₆-alkynyl)carbonyloxy, (C₂-C₆-alkynyl)carbonylthio, C₁-C₆-alkylsulfonyloxy or C₁-C₆-alkylsulfonyl, where each of these 17 radicals may, if desired, carry one, two or three substituents, selected from the group consisting of:

halogen, nitro, cyano, hydroxyl, C₃-C₆-cycloalkyl, C₁-C₆-alkoxy, C₃-C₆-cycloalkoxy, C₃-C₆-alkenyloxy, C₃-C₆-alkynyloxy, C₁-C₆-alkoxy-C₁-C₆-alkoxy, C₁-C₆-alkylthio, C₁-C₆-alkylsulfinyl, C₁-C₆-alkylsulfonyl, C₁-C₆-alkylideneaminoxy, oxo, ═N—OR¹³

phenyl, phenoxy or phenylsulfonyl, where the three last-mentioned substituents for their part may carry one, two or three substituents, in each case selected from the group consisting of halogen, nitro, cyano, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy and (C₁-C₆-alkoxy)carbonyl;

—CO—R¹⁴, —CO—OR¹⁴, —CO—SR¹⁴, —CO—N(R¹⁴)—R¹⁵, —OCO—R¹⁴, —OCO—OR^(14′), —OCO—SR^(14′), —OCO—N(R¹⁴)—R¹⁵, —N(R¹⁴)—R¹⁵ and —C(R¹⁶)═N—OR¹³;

is C(Z^(1)—R) ¹⁷, —C(═NR¹⁸)R¹⁷, C(R¹⁷)(Z²R¹⁹)(Z³R²⁰) C(R¹⁷)═C(R²¹)—CN, C(R¹⁷)═C(R²¹)—CO—R²², —CH(R¹⁷)—CH(R²¹)—COR²², —C(R¹⁷)═C(R²¹)—CH₂—CO—R²², —C(R¹⁷)═C(R²¹)—C(R²³)═C(R²⁴)—CO—R²², —C(R¹⁷)═C(R²¹)—CH₂—CH(R²⁵)—CO—R²², —CO—OR²⁶, —CO—SR²⁶, —CON(R²⁶)—OR¹³, —C≡C—CO—NHOR¹³, —C≡C—C—CO—N(R²⁶)—OR¹³, —C≡C—C—NH—OR¹³, —C≡C—CS—N(R²⁶)—OR¹³, —C(R¹⁷)═C(R²¹)—CO—NHOR¹³, —C(R¹⁷)═C(R²¹)—CO—N(R²⁶)—OR¹³, —C(R¹⁷)═C(R²¹)—CS—NHOR¹³, —C(R¹⁷)═C(R²¹)—CS—N(R²⁶)—OR¹³, —C(R¹⁷)═C(R²¹)—C(R¹⁶)═N—OR¹³, C(R¹⁶)═N—OR¹³, —C≡—C—C(R¹⁶)═NOR¹³, C(Z²R¹⁹)(Z³R²⁰)—OR²⁶, —C(Z²R¹⁹)(Z²R²⁰)SR²⁶, C(Z²R¹⁹)(Z³R²⁰)—N(R²⁷)R²⁸, —N(R²⁷)—R²⁸, —CO—N(R²⁷)—R²⁸ or C(R¹⁷)═C(R²¹)CO—N(R²⁷)R²⁸; where Z¹, Z², Z³ independently of one another are oxygen or sulfur;

R¹¹ is hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₃-C₆-alkenyl, C₃-C₆-alkynyl, C₃-C₇-cycloalkyl, or 3- to 7-membered saturated heterocyclyl containing one or more oxygen and/or sulfur atoms;

R^(11′) is hydrogen or C₁-C₆-alkyl;

R¹² is hydrogen or C₁-C₃-alkyl;

R^(12′) is hydrogen, C₁-C₃-alkyl;

R¹² and R^(12′) together are C═O;

R¹³ is hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₃-C₆-cycloalkyl, C₃-C₆-alkenyl, C₃-C₆-alkynyl, C₁-C₆-alkoxy-C₁-C₆-alkyl, cyano-C₁-C₆-alkyl, (C₁-C₆-alkoxy)carbonyl-C₁-C₆-alkyl or phenylalkyl, where the phenyl ring may be mono- to trisubstituted by halogen, cyano, nitro, C₁-C₃-alkyl, C₁-C₃-haloalkyl or C₁-C₃-alkoxy;

R¹⁴ is hydrogen, C₁-C₆-alkyl, C₃-C₆-cycloalkyl, C₃-C₆-alkenyl, C₃-C₆-alkynyl, C₁-C₆-alkoxy-C₁-C₆-alkyl, (C₁-C₆-alkoxy)carbonyl-C₁-C₆-alkyl, (C₁-C₆-alkenyloxy)carbonyl-C₁-C₆-alkyl, is phenyl or benzyl, which may be unsubstituted at the phenyl ring or mono to trisubstituted by halogen, cyano, nitro, C₁-C₃-alkyl, C₁-C₃-haloalkyl or C₁-C₃-alkoxy;

R^(14′) has the meanings of R¹⁴ with the exception of hydrogen;

R¹⁵ is hydrogen, hydroxyl, C₁-C₆-alkyl, C₁-C₆-alkoxy, (C₁-C₃-alkoxy)carbonyl-C₁-C₃-alkoxy, C₃-C₆-alkenyl or C₃-C₆-alkynyl;

R¹⁶ is hydrogen, halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₃-C₆-alkenyloxy, (C₁-C₆-alkoxy)carbonylalkoxy, C₂-C₆-alkenyl, (C₂-C₆-alkenyl)carbonyloxy, C₃-C₆-alkynyl, (C₂-C₆-alkynyl)carbonyloxy,

is phenyl, phenoxy or benzyl, where the phenyl rings of the 3 last-mentioned radicals may be unsubstituted or mono- to trisubstituted by halogen, cyano, nitro, C₁-C₃-alkyl, C₁-C₃-haloalkyl, C₁-C₃-alkoxy or (C₁-C₃-alkoxy)carbonyl;

R¹⁷ is hydrogen, cyano, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-alkoxy-C₁-C₆-alkyl or (C₁-C₆-alkoxy)carbonyl;

R¹⁸ is hydrogen, C₁-C₆-alkyl, C₃-C₆-alkenyl, C₃-C₆-alkynyl, C₃-C₆-cycloalkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy-C₁-C₆-alkyl, C₁-C₆-alkoxy, (C₁-C₆-alkoxy)carbonyl-C₁-C₆-alkyl,

is phenyl or phenyl-(C₁-C₆-alkyl), where the two last-mentioned phenyl radicals may be substituted by halogen, cyano, nitro, C₁-C₃-alkyl, C₁-C₃-haloalkyl, C₁-C₃-alkoxy or (C₁-C₃-alkoxy)carbonyl;

R¹⁹, R²⁰ independently of one another are C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₃-C₆-alkenyl, C₃-C₆-alkynyl, C₁-C₆-alkoxy-C₁-C₆-alkyl, or

R¹⁹ and R²⁰ together are a saturated 2- to 4-membered carbon chain which may carry an oxo substituent, where a carbon atom of this chain which is not adjacent to the variables Z² and Z³ may be replaced by —O—, —S—, —N═, —NH— or —N(C₁-C₆-alkyl)—, and where the carbon chain may be mono- to trisubstituted by halogen or C₁-C₆-alkyl;

R²¹ is hydrogen, cyano, halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl or C₁-C₆-alkoxy;

R²² is hydrogen, OR³¹, S—R³¹, C₁-C₆-alkyl, which may carry one or two C₁-C₆-alkoxy substituents, is C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-haloalkyl or C₃-C₆-cycloalkyl;

R²³ is hydrogen, cyano, halogen, C₁-C₆-alkyl, C₃-C₆-alkenyl or C₃-C₆-alkynyl;

R²⁴ is hydrogen, cyano, halogen, C₁-C₆-alkyl, C₁-C₆-alkoxy or C₁-C₆-haloalkyl;

R²⁵ is hydrogen, cyano or C₁-C₆-alkyl;

R²⁶, R³¹ independently of one another are hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₂-C₆-alkenyl or C₂-C₆-alkynyl, where the 4 last-mentioned groups may in each case carry one or two of the following radicals: cyano, halogen, C₁-C₆-alkoxy, C₁-C₆-alkylcarbonyl, (C₁-C₆-alkoxy)carbonyl;

or are (C₁-C₆-alkyl)carbonyl, (C₁-C₆-alkoxy)carbonyl, phenyl or phenyl-C₁-C₆-alkyl;

R²⁷, R²⁸, R²⁹, R³⁰ independently of one another are hydrogen, C₁-C₆-alkyl, C₃-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy-C₁-C₆-alkyl, C₁-C₆-alkylcarbonyl, (C₁-C₆-alkoxy)carbonyl, or

R²⁷ and R²⁸ and/or R²⁹ and R³⁰ in each case together with the common nitrogen atom are a saturated or unsaturated 4- to 7-membered azo heterocycle which, in addition to carbon ring members, may, if desired, contain an oxygen atom or an —NH group;

m is 0, 1, 2 or 3.

R⁹ is, in particular, halogen, and specifically fluorine or chlorine. R^(A) is, in particular, hydrogen, i.e., m is 0.

In particular, R¹⁰ in Q1 is:

C₁-C₆-alkoxy, C₂-C₆-alkenyloxy or C₂-C₆-alkynyloxy, where each of the 3 last-mentioned radicals may, if desired, carry one to three substituents, in each case selected from the group consisting of halogen, C₁-C₆-alkoxy, C₃-C₆-alkenyloxy, C₃-C₆-alkynyloxy, C₁-C₆-alkylsulfonyl, —CO—R¹⁴, —CO—OR¹⁴, —CO—N(R¹⁴⁾—R¹⁵, —N(R¹⁴)—R¹⁵, and —C(R¹⁶)═N—OR¹³;

—CO—R¹⁷, —C(NR¹⁸)—R¹⁷, —C(R¹⁷)(OR¹⁹)(OR²⁰), —C(R¹⁷)═C(R²¹)—CO—R²², —CH(R¹⁷)—CH(R²¹)—CO—R²², —CO—OR²⁶, —CO—N(R²⁶)—OR¹³, —C(R¹⁷)═C(R²¹)—CO—N(R²⁶)—OR¹³, —C(R¹⁶)═N—OR¹³, —C(OR¹⁹)(OR²⁰)—OR²⁶, —N(R²⁷)R²⁸, —CON(R²⁷)R²⁸ or —C(R¹⁷)═C(R²⁷)CO—N(R²⁷)R²⁸;

where R¹³ to R²² and R²⁶ to R²⁸ are as defined above,

and is specifically C₂-C₆-alkenyloxy, C₂-C₆-alkynyloxy, —C(R¹⁷)(OR¹⁹)(OR²⁰), —C(R¹⁷)═C(R²¹)—C(O)R²¹, —CH(R¹⁷)—CH(R²¹)—C(O)R²², C(O)OR²⁶, —C(O)—N(R²⁶)—OR¹³,—C(R¹⁶)═N—OR¹³ and C(O)N(R²⁷)R²⁸, in which R¹³, R¹⁶, R¹⁷, R¹⁹, R²⁰, R²¹, R²², R²⁶, R²⁷ and R²⁸ have the meanings given above and in particular those mentioned below:

R¹³ is C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₃-C₆-alkenyl, C₃-C₆-haloalkenyl, C₃-C₆-alkynyl, C₁-C₆-cyanoalkyl and C₁-C₆-alkoxycarbonyl-C₁-C₆-alkyl;

R¹⁶ is hydrogen, C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₆-alkoxycarbonyl-C₁-C₆-alkyl, C₁-C₆-alkoxycarbonyl-C₁-C₆-alkoxy and phenoxycarbonyl-C₁-C₆-alkoxy;

R¹⁷ is hydrogen, C₁-C₆-alkyl;

R¹⁹ and R²⁰ independently of one another are C₁-C₆-alkyl;

R²¹ is hydrogen, halogen, C₁-C₆-alkyl;

R²² is hydroxyl, C₁-C₆-alkoxy, C₁-C₆-alkylthio, C₁-C₆-alkoxycarbonyl-C₁-C₆-alkyl;

R²⁶ is C₁-C₆-alkyl, C₃-C₆-haloalkyl, C₃-C₆-alkenyl, C₃-C₆-alkynyl, C₁-C₆-alkoxycarbonyl-C₁-C₆-alkyl, C₃-C₆-alkenyloxycarbonyl-C₁-C₆-alkyl, C₃-C₆-alkynyloxycarbonyl-C₁-C₆-alkyl, C₁-C₆-alkoxyalkyl;

R²⁷ is hydrogen, C₁-C₆-alkyl;

R²⁸ is hydrogen, C₁-C₆-alkyl, C₁-C₆-alkoxy,

or R²⁷ and R²⁸ together are a 6-membered saturated azaheterocycle which may have one or two non-adjacent oxygen atoms in the ring.

To prepare the compounds of the formula V from the compounds of the formulae I and VI, it is preferred to add the isocyanate or the isothiocyanate of the formula VI over a period of 5 to 120 min, preferably within 10 to 30 min, to the compound I, which is preferably initially charged as a mixture with one of the solvents mentioned in step 1 of the preparation of I. However, it is also possible to initially charge the compound VI, preferably in one of the abovementioned solvents, and to add the compound I thereto.

The reaction conditions correspond essentially to the reaction conditions mentioned in step 1 of the preparation of I.

The compound VI is preferably added to the compound I, or the compound I to the compound VI, at temperatures in the range from 0 to 50° C., in particular from 10 to 25° C. For the reaction to go to completion, the components are allowed extra reaction time of approximately 0.5 to 20 h, in particular 1 to 10 h, preferably at temperatures in the range from 20 to 80° C.

The reaction is preferably carried out under inert conditions, i.e. with exclusion of oxygen, for example under inert gases, in a dry, i.e. substantially water- and alcohol-free, solvent.

The reaction can be accelerated by adding a Lewis acid to activate the isocyanate or isothiocyanate of the formula VI. Lewis acids which are customary for this purpose are organotin compounds, for example, di-C₂-C₈-alkyltin(IV) dicarboxylates, such as di-n-butyltin(IV) diacetate. The Lewis acid is customarily employed in an amount of up to 15% by weight, preferably from 1 to 10% by weight, and in particular from 2 to 5% by weight, based on the isocyanate or the isothiocyanate of the formula VI.

The reaction can also be accelerated by addition of nucleophilic bases, for example pyridine, α-, β- or γ-picoline, quinoline, 4-dimethylaminopyridine or 4-pyrrolidinopyridine. The nucleophilic base is usually employed in an amount of up to 15% by weight, preferably from 0.5 to 10% by weight and in particular from 0.5 to 5% by weight, based on the compound VI.

The substituted ureas of the formula V obtainable in this manner are, on the one hand, effective herbicides. However, they are also suitable starting materials for preparing herbicides having a triazoline-2,5-dione structure (compounds of the formula VIII) if R is a radical which can be cleaved off from the compounds V, for example by hydrolysis.

Examples of hydrolysable radicals R are COOH, CHO, C(O)OR³, C(S)OR³, C(S)SR³ and C(O)SR³.

The hydrolysis of the N-substituted ureas with diazine structure (compounds V) to the compounds VII having an unsubstituted nitrogen in the 3-position succeeds in a simple manner by hydrolysis with water.

The reaction is advantageously carried out in the presence of an auxiliary base. The reaction temperature is usually in the range from 10 to 100° C., preferably in the range from 20 to 80° C.

The reaction is preferably carried out in a solvent, for example a water-miscible solvent, e.g. a C₁-C₄-alcohol, such as ethanol or methanol, a cyclic ether, such as tetrahydrofuran or dioxane, an amide, such as dimethylformamide, dimethylacetamide, N-methylpyrrolidone; dimethylsulfoxide, acetonitrile, a mixture of the abovementioned solvents with one another or a mixture with water, or in water itself.

Suitable bases are all of the abovementioned bases. Preference is given to alkali metal or alkaline earth metal hydroxide, particularly preferably sodium hydroxide.

The base is advantageously employed in a molar ratio of from 0.9 to 1.4, preferably from 0.95 to 1.2, particularly preferably from 0.98 to 1.15, for the ratio of substituted urea Ib to base.

The resulting compounds VII can be cyclized to the compounds VIII in accordance with the scheme below. Compounds VII and VIII have herbicidal activities.

The cyclization of the 3-(arylcarbamoyl)tetrahydro-4H-1,3,4-oxa-(or thia)diazines VII is carried out using phosgene or a phosgene substitute, for example diphosgene (ClC(═O)OCCl₃), advantageously in the presence of one of the abovementioned anhydrous solvents, at temperatures in the range from −10 to 120° C., preferably from 0 to 80° C., particularly preferably from 10 to 60° C.

The phosgene is advantageously introduced at from 10 to 60° C. and with stirring into a mixture of VII and an amount of from 0.5 to 5% by weight, based on the starting material, of activated carbon as catalyst, in one of the abovementioned anhydrous solvents, over a period of from 0.5 to 20 hours, preferably from 1 to 12 hours.

The reaction can additionally be accelerated by a basic amide catalyst, for example DMF, which can usually be employed in an amount of from 0.3 to 10% by weight, based on the starting material. Suitable basic catalysts are also organic bases, such as triethylamine, tri-n-propylamine, N,N-dimethylaniline or N,N-dimethylcyclohexylamine. Preference is also given to using pyridine, if appropriate directly as solvent.

In place of phosgene, it is also possible to use diphosgene. The diphosgene is advantageously added with stirring at from 0 to −5° C. and over a period of from 2 to 20 min to the mixture of the starting material and one of the abovementioned solvents, if appropriate with addition of activated carbon, DMF or the organic base, and the mixture is allowed to warm to 10° C. over a period of 1 hour and then stirred at 10-60° C. for another 1 to 12 hours. The molar amount of phosgene or diphosgene is from 0.98 to 5, preferably from 1 to 3, particularly preferably from 1 to 1.3 mol per mole of starting material.

The concentration of the starting materials in the solvent is generally from 0.1 to 5 mol/l, preferably from 0.2 to 2 mol/l.

The reaction can be carried out under atmospheric pressure or superatmospheric pressure, continuously or batchwise.

The examples given below serve to illustrate the invention.

EXAMPLE 1 Methyl Tetrahydro-4H-1,3,4-oxadiazine-4-carboxylate (Compound According to the Invention)

a) Methyl N-Amino-N-2-hydroxyethylcarbamate (Compound IV.1a—See Table 3)

At 0-5° C., 248.4 g (2.628 mol) of methyl chloroformate were added with stirring, over a period of 30 min, to a mixture of 200 g (2.628 mol) of 2-hydrazinoethanol and 266 g (2.628 mol) of triethylamine in 1600 ml of methylene chloride. After 3 h of stirring at from 3 to 22 C, the resulting hydrochloride was removed by filtration and washed with THF. The filtrates were combined. The filter cake was suspended in 800 ml of THF and filtered again. This filtrate, too, was combined with the previous filtrate. The combined filtrates were concentrated under reduced pressure. This gave 366 g of the title compound as colorless oil having an HPLC purity of 95.3%, corresponding to a yield of 98.9% of theory. According to GC, the purity was 85.2%.

¹H-NMR (400 MHZ, d₆-DMSO) δ (ppm): 4.4-4.8 (broad/3H) NH₂/OH; 3.6 (s/3H) CH₃O; 3.52 (t/2H) and 3.35 (t/2H) CH₂—CH₂.

b) Methyl Tetrahydro-4H-1,3,4-oxadiazine-4-carboxylate (Compound Ib.1—See Table 4)

At 22° C., 22.4 g (0.746 mol) of paraformaldehyde were added with stirring, over a period of 2 min to a mixture of 100 g (0.746 mol) of methyl N-amino-N-2-hydroxyethylcarbamate in 1500 ml of methylene chloride. After addition of 8.5 g (0.045 mol) of p-toluenesulfonic acid, the mixture was stirred at 42° C. for 21 h, until the precipitate had dissolved, and was then cooled to 20° C., and magnesium sulfate was added. The mixture was filtered and the filtrate was concentrated under reduced pressure. This gave 111.8 g of the title compound as a colorless resin with a GC purity of 85%, corresponding to a yield of 85.8% of theory.

¹H-NMR (500 MHZ, CF₃CO₂D) δ (ppm): 5.09 (s/2H) CH₂; 4.02 (s/3H); CH₃O; 3.8-4.25 (m/4H) CH₂CH₂; IR ν (C═O) 1703 cm⁻¹.

The intermediates 2a to 15a listed in Table 3 were obtained analogously to Example la. Refractive index (n²³/_(D)) and/or characteristic IR bands (NH, CO) are stated in Table 3.

TABLE 3

Compound IV No. R n^(23/) _(D) ν [cm⁻¹] Yield [%] 1a CO₂CH₃ 98.9 2a CO₂C₂H₅ C═O 1695 cm⁻¹, 88 NH₂ 3336 cm⁻¹ 3a C(O)SCH₃ 1.5458 85 4a C(O)SC₂H₅ 1.5345 86 5a CO₂-i-C₃H₇ C═O 1694 cm⁻¹, 69 NH₂ 3338 cm⁻¹ 6a CO₂-t-C₄H₉ 7a CO₂-phenyl 8a CO₂-p-Cl-phenyl 9a CO₂-benzyl C═O 1706 cm⁻¹, 62 NH₂ 3336 cm⁻¹ 10a  C(S)OCH₃ 11a  CO₂-n-C₈H₁₇ 12a  CO₂CH₂CH₂Cl 1.4988 C═O 1706 cm⁻¹ 65 13a  CO₂-Cyclopentyl 1.4981 C═O 1695 cm⁻¹ 50 14a  CO₂-n-C₁₄H₁₉ C═O 1700 cm⁻¹ 88 15a  COCH₃ 1.4938 22 n^(23/) _(D) refractive index ν [cm⁻¹] IR absorption

The target compounds of the formula Ib (compounds Ib.2b to Ib.15b) listed in Table 4 were obtained analogously to Example lb. Refractive index, characteristic IR bands (NH, CO) and/or ¹H-NMR data are given in Table 4.

TABLE 4 (Ia)

n^(23/) _(D) Ex. bp [° C./mbar] ¹H-NMR Yield No. R mp [° C.] ν [cm⁻¹] [δ (ppm)] [%] 1b CO₂CH₃   —   — supra 85.8 2b CO₂C₂H₅ 100-105/0.5 C═O: 1701 4.05 (q/2H), 78 O—CH₂—C; 1.18 (t/3H) CH₃ 3b C(O)SCH₃ 103-111/0.4 C═O: 1659 75 1.5542 4b C(O)SC₂H₅ 1.5428 C═O: 1657 74 5b CO₂-i-C₃H₇ C═O: 1702 61 6b CO₂-t-C₄H₉ 7b CO₂-phenyl 8b CO₂-p-Cl-phenyl 9b CO₂-benzyl 7.4-7.24 43 (m, 5H) 5.1 (s, 2H) 10b  C(S)OCH₃ 11b  CO₂-n-C₈H₁₇ 12b  CO₂CH₂CH₂Cl 1.5130 C═O 1709 53 13b  CO₂-cyclopentyl 145-150/0.5 C═O 1700 51 14b  CO₂-n-C₁₄H₂₉ 77-81 59 15b  COCH₃ C═O 1683 34 n^(23/) _(D) refractive index mp melting point bp boiling point at given pressure

USE EXAMPLE 1 Process According to the Invention

1 a) Methyl 3-[N-(4′-Chloro-2′-fluoro-5′-propargyloxyphenyl)amino-carbonyl]tetrahydro-4H-1,3,4-oxadiazine-4-carboxylate

Over a period of 10 min, 5.7 g (25.25 mmol) of 4-chloro-2-fluoro-5-propargyloxyphenylisocyanate in 50 ml THF were added with stirring, at 22° C., to a mixture of 3.7 g (25.25 mmol) of the compound from Example 1b in 150 ml THF, resulting in the reaction solution warming to 25° C. over a period of 1 h.

After 12 h at 22° C., the reaction solution was concentrated and chromatographed over silica gel using methylene chloride/ether 2:1. The concentration gave 7.4 g (79% of theory) of the title compound of m.p. 130° C.

1 b) 3-[N-(4-Chloro-2-fluoro-5-propargyloxyphenyl)amino-carbonyl]tetrahydro-4H-1,3,4-oxadiazine

Over a period of 20 min, 0.41 g (10.35 mmol) of sodium hydroxide dissolved in 25 ml of water were added with stirring, at 60-70° C., to a solution of 3.5 g (9.42 mmol) of the compound from Example la in 75 ml of ethanol. According to thin-layer chromatography, the reaction went to completion. The mixture was cooled and substantially concentrated under reduced pressure. 50 ml of water were added and the mixture was then acidified using 1 N hydrochloric acid, resulting in evolution of gas with slight foaming and formation of a precipitate. The aqueous phase was extracted three times with methylene chloride and the combined extracts were dried under magnesium sulfate and concentrated to dryness under reduced pressure. This gave 3.0 g of a colorless powder of m.p. 138-142° C. According to GC/MS, the powder contained 1.71 g of the title compound (yield: 58% of theory).

The compound 1b and the comparative product below can be cyclized to herbicidal fused triazoles using, according to the prior art (WO 94/10173), phosgene or a phosgene substitute.

COMPARATIVE EXAMPLE (WO 94/10173) Tetrahydro-4-[N-(4-chloro-2-fluoro-5-propargyloxyphenyl)amino-carbonyl-4H-1,3,4-oxadiazine

5.0 g (16.57 mmol of N-amino-N-2-hydroxyethyl-N′-(4-chloro-2-fluoro-5-propargyloxy-phenyl)urea, 1.5 g (12.2 mmol) of 37% strength formaldehyde and 0.5 g of p-toluenesulfonic acid were, at 42° C., stirred in methylene chloride for 17 h, using a Dean-Stark separator. After cooling, the reaction mixture was partially concentrated under reduced pressure and then chromatographed over 200 ml of silica gel, using methylene chloride and then ethyl acetate. This gave 3.6 g of a substance mixture which, according to TLC, HPLC and NMR, consisted of 6 to 7 substances. According to HPLC analysis with independently prepared material for comparison, 0.74 g (14.2% of theory) of the title compound was present.

When the column was rinsed with methanol, only p-toluenesulfonic acid could be isolated.

Thus, the process according to the invention gives compounds VII in considerably better yields, and therefore provides better access to the herbicides of the formula VIII. 

We claim:
 1. An N-substituted perhydro-3,4-diazine of formula

in which Z is O; R^(A) is hydroxyl, CO₂R¹, halogen, cyano, C(O)NR¹ ₂, OR², C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₃-C₆-alkenyl, C₃-C₆-alkynyl, COR¹, S(O)_(n)R¹where n=0, 1 or 2, or C(O)SR¹; R is CO₂H, CHO, CN, C(O)OR³, C(S)OR³, C(O)SR³, C(S)SR³, C(O)NR⁴R⁵, C(S)NR⁴R⁵, C(O)NHCO₂R⁶, C(O)NHSO₂R⁶, C(O)NHSO₃R⁶, C(O)R², P(O)R¹OR¹, P(O)(OR¹)₂, S(O)_(n)R² where n=0, 1, or 2 or SO₂NHR¹; m has the value 0, 1, 2 or 3 and in which the variables R¹ to R⁷ are as defined below: R¹ is hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₃-alkoxy-C₁-C₃-alkyl, C₃-C₆-alkenyl or C₃-C₆-alkynyl; R² is C₁-C₆-alkyl, C₃-C₆-cycloalkyl, C₃-C₆-alkenyl, C₃-C₆-alkynyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy-C₁-C₆-alkyl, hydroxycarbonyl-C₁-C₆-alkyl, C₁-C₆-alkoxycarbonyl-C₁-C₆-alkyl, C₁-C₆-alkylthio-C₁-C₆-alkyl, C₁-C₆-alkylsulfinyl-C₁-C₆-alkyl, C₁-C₆-alkylsulfonyl-C₁-C₆-alkyl, C₃-C₆-cycloalkyl-C₁-C₆-alkyl, C₃-C₆-alkenyloxycarbonyl-C₁-C₆-alkyl, C₃-C₆-alkynyloxycarbonyl-C₁-C₆-alkyl, C₃-C₆-cycloalkoxy-C₁-C₆-alkyl, C₃-C₆-alkenyloxy-C₁-C₆-alkyl, C₃-C₆-alkynyloxy-C₁-C₆-alkyl, C₁-C₆-haloalkoxy-C₁-C₆-alkyl, C₃-C₆-haloalkenyloxy-C₁-C₆-alkyl, C₃-C₆-haloalkynyloxy-C₁-C₆-alkyl, C₃-C₆-cycloalkyl-C₁-C₆-thioalkyl, C₃-C₆-alkenylthio-C₁-C₆-alkyl, C₃-C₆-alkynylthio-C₁-C₆-alkyl, cyano-C₁-C₆-alkyl, C₃-C₆-halocycloalkyl-C₁-C₆-alkyl, halo-C₂-C₆-alkenyl, C₁-C₆-alkoxy-C₃-C₆-alkenyl, C₁-C₆-haloalkoxy-C₃-C₆-alkenyl, C₁-C₆-alkylthio-C₃-C₆-alkenyl, C₃-C₆-haloalkynyl, C₁-C₆-alkoxy-C₃-C₆-alkynyl, C₁-C₆-haloalkoxy-C₃-C₆-alkynyl, C₁-C₆-alkylthio-C₃-C₆-alkynyl, C₁-C₆-alkylcarbonyl, CHR¹COR⁷, CHR¹P(O)(OR⁷)₂, P(O)(OR⁷)₂, CHR¹P(S)(OR⁷)₂, CHR¹C(O)NR⁴R⁵, CHR¹C(O)NH₂, or R² is phenyl, pyridyl, benzyl, phenoxy-C₁-C₆-alkyl, benzyloxy-C₁-C₆-alkyl, where the phenyl or pyridyl groups of the five last-mentioned substituents may be substituted by halogen, C₁-C₄-alkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkyl, R³ is C₁-C₁₅-alkyl, C₃-C₈-cycloalkyl, C₂-C₁₀-alkenyl, C₃-C₁₀-alkynyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy-C₁-C₆-alkyl, C₁-C₆-alkylthio-C₁-C₆-alkyl, C₁-C₆-alkylsulfinyl-C₁-C₆-alkyl, C₁-C₆-alkylsulfonyl-C₁-C₆-alkyl, C₁-C₃-alkoxy-C₁-C₃-alkoxy-C₁-C₃-alkyl, C₃-C₆-cycloalkyl-C₁-C₆-alkyl, carboxyl-C₁-C₆-alkyl, C₁-C₆-alkoxycarbonyl-C₁-C₆-alkyl, C₁-C₆-alkoxycarbonyl-C₂-C₆-alkenyl, C₃-C₆-alkenyloxycarbonyl-C₁-C₆-alkyl, C₃-C₆-alkynyloxycarbonyl-C₁-C₆-alkyl, C₃-C₈-cycloalkoxy-C₁-C₆-alkyl, C₃-C₆-alkenyloxy-C₁-C₆-alkyl, C₃-C₆-alkynyloxy-C₁-C₆-alkyl, C₁-C₆-haloalkoxy-C₁-C₆-alkyl, C₃-C₆-haloalkenyloxy-C₁-C₆-alkyl, C₃-C₆-haloalkynyloxy-C₁-C₆-alkyl, C₃-C₆-cycloalkyl-C₁-C₆-thioalkyl, C₃-C₆-alkenylthio-C₁-C₆-alkyl, C₃-C₆-alkynylthio-C₁-C₆-alkyl, cyano-C₁-C₆-alkyl, C₃-C₆-halocycloalkyl-C₁-C₆-alkyl, halo-C₃-C₆-alkenyl, C₁-C₆-alkoxy-C₃-C₆-alkenyl, C₁-C₆-haloalkoxy-C₃-C₆-alkenyl, C₁-C₆-alkylthio-C₃-C₆-alkenyl, C₃-C₆-haloalkynyl, C₁-C₆-alkoxy-C₃-C₆-alkynyl, C₁-C₆-haloalkoxy-C₃-C₆-alkynyl, C₁-C₆-alkylthio-C₃-C₆-alkynyl, or R³ is CHR¹COR⁷, CHR¹P(O)(OR⁷)₂, P(O)(OR⁷)₂, CHR¹P(S)(OR⁷)₂, CHR¹C(O)NR⁴R⁵, CHR¹C(O)NH₂, phenoxy-C₁-C₆-alkyl, benzyloxy-C₁-C₆-alkyl, where the phenyl groups of the two last-mentioned substituents may be substituted by halogen, C₁-C₄-alkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkyl; or R³ is phenyl, pyridyl, naphthyl, quinolyl, quinazolyl, quinoxalyl, 1-methylindolyl, 1-methylbenzimidazolyl, 2-methylindazolyl, benzofuranyl, benzothienyl, benzoxazolyl, benzothiazolyl, benzyl, where the 14 last-mentioned substituents may carry, in adjacent positions, a divalent substituent selected from the group consisting of methylenedioxy, difluoromethylenedioxy, chlorofluoromethylenedioxy and dichloromethylenedioxy, or may in each case be mono- to pentasubstituted by halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio, amino, C₁-C₄-monoalkylamino, C₁-C₄-dialkylamino, C₃-C₆-cycloalkyl, C₁-C₄-alkoxycarbonyl, C₁-C₄-alkoxycarbonyl-C₁-C₄-alkyl, hydroxyl, nitro or cyano; R⁴ is hydrogen, C₁-C₆-alkyl or C₁-C₆-alkoxy; R⁵, R⁶ independently of one another are hydrogen, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy-C₁-C₆-alkyl, C₁-C₆-alkoxycarbonyl-C₁-C₆-alkyl, C₁-C₆-alkoxycarbonyl-C₂-C₆-alkenyl, where the alkenyl chain may additionally carry one to three halogen and/or cyano radicals, benzyl which, in adjacent positions of the phenyl ring, may carry a divalent substituent selected from the group consisting of methylenedioxy, difluoromethylenedioxy, chlorofluoromethylenedioxy and dichloromethylenedioxy, or which may be mono- to pentasubstituted by halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio, C₃-C₆-cycloalkyl, C₁-C₄-alkoxycarbonyl, C₁-C₄-alkoxycarbonyl-C₁-C₄-alkyl, hydroxyl, nitro or cyano, or R⁴ and R⁵ together with the nitrogen atom to which they are attached are a saturated or unsaturated 4- to 7-membered azaheterocycle which, in addition to carbon ring members, optionally has one of the following members: —O—, —S—, —N═, —NH— or —N(C₁-C₆-alkyl)—; R⁷ is hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₃-alkoxy-C₁-C₃-alkyl, C₂-C₆-cyanoalkyl, C₃-C₆-alkenyl or C₃-C₆-alkynyl.
 2. The perhydrodiazine of formula I defined in claim 1 in which R¹ is hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₃-alkoxy-C₁-C₃-alkyl, C₃-C₆-alkenyl or C₃-C₆-alkynyl; R² is C₁-C₆-alkyl, C₃-C₆-cycloalkyl, C₃-C₆-alkenyl, C₃-C₆-alkynyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy-C₂-C₆-alkyl, C₁-C₆-alkoxycarbonyl-C₁-C₆-alkyl, C₁-C₆-alkylthio-C₁-C₆-alkyl, C₃-C₆-alkenyloxycarbonyl-C₁-C₆-alkyl, C₃-C₆-alkynyloxycarbonyl-C₁-C₆-alkyl, C₃-C₆-alkenyloxy-C₁-C₆-alkyl, C₃-C₆-alkynyloxy-C₁-C₆-alkyl, C₁-C₆-haloalkoxy-C₁-C₆-alkyl, cyano-C₁-C₆-alkyl, halo-C₂-C₆-alkenyl, halo-C₃-C₆-alkynyl, C₁-C₆-alkylcarbonyl, CHR₁COR⁷, P(O)(OR⁷)₂, CHR¹P(S)(OR⁷)₂, CHR¹C(O)NR⁴R⁵, CHR¹C(O)NH₂, or R² is benzyl, phenyl, phenoxy-C₁-C₆-alkyl or benzyloxy-C₁-C₆-alkyl, where the four last-mentioned substituents may be substituted by halogen, C₁-C₄-alkyl or C₁-C₄-haloalkyl; R³ is C₁-C₁₅-alkyl, C₃-C₈-cycloalkyl, C₂-C₁₀-alkenyl, C₃-C₁₀-alkynyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy-C₁-C₆-alkyl, C₁-C₆-alkylthioalkyl, C₁-C₆-alkoxycarbonyl-C₁-C₆-alkyl, C₃-C₆-alkenyloxycarbonyl-C₁-C₆-alkyl, C₃-C₆-alkynyloxycarbonyl-C₁-C₆-alkyl, C₃-C₆-alkenyloxy-C₁-C₆-alkyl, C₁-C₆-haloalkoxy-C₁-C₆-alkyl, cyano-C₁-C₆-alkyl, halo-C₃-C₆-alkenyl, C₁-C₆-alkoxy-C₃-C₆-alkenyl, C₁-C₆-alkoxy-C₃-C₆-alkynyl, CHR¹COR⁷, P(O)(OR⁷)₂, CHR¹P(S)(OR⁷)₂, CHR¹C(O)NR⁴R⁵, CHR¹C(O)NH₂, or R³ is benzyl, phenyl, phenoxy-C₁-C₆-alkyl or benzyloxy-C₁-C₆-alkyl, where the four last-mentioned substituents may be substituted by halogen, C₁-C₄-alkyl or C₁-C₄-haloalkyl; R⁴ is hydrogen, C₁-C₆-alkyl or C₁-C₆-alkoxy; R⁵, R⁶ independently of one another are hydrogen, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy-C₁-C₆-alkyl, C₁-C₆-alkoxycarbonyl-C₁-C₆-alkyl, C₁-C₆-alkoxycarbonyl-C₂-C₆-alkenyl, benzyl which may be mono- to pentasubstituted by halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio, C₁-C₄-alkoxycarbonyl, C₁-C₄-alkoxycarbonyl-C₁-C₄-alkyl, nitro or cyano, or R⁴ and R⁵ together with the common nitrogen atom are a saturated or unsaturated 4- to 7-membered azaheterocycle which, in addition to the carbon ring members optionally has one of the following members: —O—, —S—, —N═, —NH— or —N(C₁-C₆-alkyl)—; R⁷ is hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₃-alkoxy-C₁-C₃-alkyl, C₂-C₆-cyanoalkyl, C₃-C₆-alkenyl or C₃-C₆-alkynyl.
 3. The perhydrodiazine of formula I defined in claim 1 in which R is selected from C(O)OR³, C(S)OR³, C(O)SR³, C(S)SR³.
 4. The perhydrodiazine of formula I defined in claim 1 in which m has the value
 0. 5. A process for preparing the perhydrodiazine of formula I defined in claim 1, which comprises at least two successive reaction steps, where, in a first reaction step, a substituted hydrazine of formula II

is reacted with an acid compound of formula III R—G  (III) in which G is a nucleophilically displaceable leaving group, or R—G is a compound of formula R⁵—N═C═X or of formula R^(2a)(R^(2b))C═C═X in which X is O or S and R^(2a)(R^(2b))C—H is the radical R², and the resulting hydrazide compound of formula IV

is, in a second step, cyclized with formaldehyde in the presence of an acid to give the perhydrodiazines of formula I, and optionally further derivatizing R.
 6. A process for preparing an urea of formula V

in which X is O or S; Q is a C₆-C₁₄-aromatic radical which is at least monosubstituted and/or attached via two adjacent carbon atoms to a saturated or unsaturated 4- to 7-membered cycle which, in addition to the carbon ring members, optionally has one, two or three members selected from the group consisting of: —O—, —S—, —S(O)₂—, —N═, —NH— and —N(C₁-C₆-alkyl)—; Z is O; R^(A) is hydroxyl, CO₂R¹, halogen, cyano, C(O)NR¹ ₂, OR², C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₃-C₆-alkenyl, C₃-C₆-alkynyl, COR¹, S(O)_(n)R¹ where n=0, 1 or 2, or C(O)SR¹; R is CO₂H, CHO, CN, C(O)OR³, C(S)OR³, C(O)SR³, C(S)SR³, C(O)NR⁴R⁵, C(S)NR⁴R⁵, C(O)NHCO₂R⁶, C(O)NHSO₂R⁶, C(O)NHSO₃R⁶, C(O)R², P(O)R¹OR¹, P(O)(OR¹)₂, S(O)_(n)R² where n=0, 1, or 2 or SO₂NHR¹; m has the value 0, 1, 2 or 3; and in which the variables R¹ to R⁷ are as defined below: R¹ is hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₃-alkoxy-C₁-C₃-alkyl, C₃-C₆-alkenyl or C₃-C₆-alkynyl; R² is C₁-C₆-alkyl, C₃-C₆-cycloalkyl, C₃-C₆-alkenyl, C₃-C₆-alkynyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy-C₁-C₆-alkyl, hydroxycarbonyl-C₁-C₆-alkyl, C₁-C₆-alkoxycarbonyl-C₁-C₆-alkyl, C₁-C₆-alkylthio-C₁-C₆-alkyl, C₁-C₆-alkylsulfinyl-C₁-C₆-alkyl, C₁-C₆-alkylsulfonyl-C₁-C₆-alkyl, C₃-C₆-cycloalkyl-C₁-C₆-alkyl, C₃-C₆-alkenyloxycarbonyl-C₁-C₆-alkyl, C₃-C₆-alkynyloxycarbonyl-C₁-C₆-alkyl, C₃-C₆-cycloalkoxy-C₁-C₆-alkyl, C₃-C₆-alkenyloxy-C₁-C₆-alkyl, C₃-C₆-alkynyloxy-C₁-C₆-alkyl, C₁-C₆-haloalkoxy-C₁-C₆-alkyl, C₃-C₆-haloalkenyloxy-C₁-C₆-alkyl, C₃-C₆-haloalkynyloxy-C₁-C₆-alkyl, C₃-C₆-cycloalkyl-C₁-C₆-thioalkyl, C₃-C₆-alkenylthio-C₁-C₆-alkyl, C₃-C₆-alkynylthio-C₁-C₆-alkyl, cyano-C₁-C₆-alkyl, C₃-C₆-halocycloalkyl-C₁-C₆-alkyl, halo-C₂-C₆-alkenyl, C₁-C₆-alkoxy-C₃-C₆-alkenyl, C₁-C₆-haloalkoxy-C₃-C₆-alkenyl, C₁-C₆-alkylthio-C₃-C₆-alkenyl, C₃-C₆-haloalkynyl, C₁-C₆-alkoxy-C₃-C₆-alkynyl, C₁-C₆-haloalkoxy-C₃-C₆-alkynyl, C₁-C₆-alkylthio-C₃-C₆-alkynyl, C₁-C₆-alkylcarbonyl, CHR¹COR⁷, CHR¹P(O)(OR⁷)₂, P(O)(OR⁷)₂, CHR¹P(S)(OR⁷)₂, CHR¹C(O)NR⁴R⁵, CHR¹C(O)NH₂, or R² is phenyl, pyridyl, benzyl, phenoxy-C₁-C₆-alkyl, benzyloxy-C₁-C₆-alkyl, where the phenyl or pyridyl groups of the five last-mentioned substituents may be substituted by halogen, C₁-C₄-alkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkyl; R³ is C₁-C₁₅-alkyl, C₃-C₈-cycloalkyl, C₂-C₁₀-alkenyl, C₃-C₁₀-alkynyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy-C₁-C₆-alkyl, C₁-C₆-alkylthio-C₁-C₆-alkyl, C₁-C₆-alkylsulfinyl-C₁-C₆-alkyl, C₁-C₆-alkylsulfonyl-C₁-C₆-alkyl, C₁-C₃-alkoxy-C₁-C₃-alkoxy-C₁-C₃-alkyl, C₃-C₆-cycloalkyl-C₁-C₆-alkyl, carboxyl-C₁-C₆-alkyl, C₁-C₆-alkoxycarbonyl-C₁-C₆-alkyl, C₁-C₆-alkoxycarbonyl-C₂-C₆-alkenyl, C₃-C₆-alkenyloxycarbonyl-C₁-C₆-alkyl, C₃-C₆-alkynyloxycarbonyl-C₁-C₆-alkyl, C₃-C₈-cycloalkoxy-C₁-C₆-alkyl, C₃-C₆-alkenyloxy-C₁-C₆-alkyl, C₃-C₆-alkynyloxy-C₁-C₆-alkyl, C₁-C₆-haloalkoxy-C₁-C₆-alkyl, C₃-C₆-haloalkenyloxy-C₁-C₆-alkyl, C₃-C₆-haloalkynyloxy-C₁-C₆-alkyl, C₃-C₆-cycloalkyl-C₁-C₆-thioalkyl, C₃-C₆-alkenylthio-C₁-C₆-alkyl, C₃-C₆-alkynylthio-C₁-C₆-alkyl, cyano-C₁-C₆-alkyl, C₃-C₆-halocycloalkyl-C₁-C₆-alkyl, halo-C₃-C₆-alkenyl, C₁-C₆-alkoxy-C₃-C₆-alkenyl, C₁-C₆-haloalkoxy-C₃-C₆-alkenyl, C₁-C₆-alkylthio-C₃-C₆-alkenyl, C₃-C₆-haloalkynyl, C₁-C₆-alkoxy-C₃-C₆-alkynyl, C₁-C₆-haloalkoxy-C₃-C₆-alkynyl, C₁-C₆-alkylthio-C₃-C₆-alkynyl, or R³ is CHR¹COR⁷, CHR¹P(O)(OR⁷)₂, P(O)(OR⁷)₂, CHR¹P(S)(OR⁷)₂, CHR¹C(O)NR⁴R⁵, CHR¹C(O)NH₂, phenoxy-C₁-C₆-alkyl, benzyloxy-C₁-C₆-alkyl, where the phenyl groups of the two last-mentioned substituents may be substituted by halogen, C₁-C₄-alkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkyl; or R³ is phenyl, pyridyl, naphthyl, quinolyl, quinazolyl, quinoxalyl, 1-methylindolyl, 1-methylbenzimidazolyl, 2-methylindazolyl, benzofuranyl, benzothienyl, benzoxazolyl, benzothiazolyl, benzyl, where the 14 last-mentioned substituents may carry, in adjacent positions, a divalent substituent selected from the group consisting of methylenedioxy, difluoromethylenedioxy, chlorofluoromethylenedioxy and dichloromethylenedioxy, or may in each case be mono- to pentasubstituted by halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio, amino, C₁-C₄-monoalkylamino, C₁-C₄-dialkylamino, C₃-C₆-cycloalkyl, C₁-C₄-alkoxycarbonyl, C₁-C₄-alkoxycarbonyl-C₁-C₄-alkyl, hydroxyl, nitro or cyano; R⁴ is hydrogen, C₁-C₆-alkyl or C₁-C₆-alkoxy; R⁵, R⁶ independently of one another are hydrogen, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy-C₁-C₆-alkyl, C₁-C₆-alkoxycarbonyl-C₁-C₆-alkyl, C₁-C₆-alkoxycarbonyl-C₂-C₆-alkenyl, where the alkenyl chain may additionally carry one to three halogen and/or cyano radicals, benzyl which, in adjacent positions of the phenyl ring, may carry a divalent substituent selected from the group consisting of methylenedioxy, difluoromethylenedioxy, chlorofluoromethylenedioxy and dichloromethylenedioxy, or which may be mono- to pentasubstituted by halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio, C₃-C₆-cycloalkyl, C₁-C₄-alkoxycarbonyl, C₁-C₄-alkoxycarbonyl-C₁-C₄-alkyl, hydroxyl, nitro or cyano, or R⁴ and R⁵ together with the nitrogen atom to which they are attached are a saturated or unsaturated 4- to 7-membered azaheterocycle which, in addition to carbon ring members, optionally has one of the following members: —O—, —S—, —N═, —NH— or —N(C₁-C₆-alkyl)—, and R⁷ is hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₃-alkoxy-C₁-C₃-alkyl, C₂-C₆-cyanoalkyl, C₃-C₆-alkenyl or C₃-C₆-alkynyl; which comprises reacting the perhydrodiazine of formula I defined in claim 1 with an isocyanate or an isothiocyanate of formula VI Q—N═C═X  (VI). 